Displaying publications 21 - 40 of 63 in total

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  1. Fulltext Characterisation and Evaluation of Trimesic Acid Derivatives as Disulphide Cross-Linked Polymers for Potential Colon Targeted Drug Delivery
    Mat Yusuf SNA, Ng YM, Ayub AD, Ngalim SH, Lim V
    Polymers (Basel), 2017 Jul 27;9(8).
    PMID: 30970988 DOI: 10.3390/polym9080311
    Discovery and use of biocompatible polymers offers great promise in the pharmaceutical field, particularly in drug delivery systems. Disulphide bonds, which commonly occur in peptides and proteins and have been used as drug-glutathione conjugates, are reductively cleaved in the colon. The intrinsic stability of a disulphide relative to thiol groups is determined by the redox potential of the environment. The objective of this study was to synthesise a trimesic acid-based disulphide cross-linked polymer that could potentially be used for targeted delivery to the colon. The monomer was synthesised by an amide coupling reaction between trimesic acid and (triphenylmethyl) thioethylamine using a two-step synthesis method. The s-trityl group was removed using a cocktail of trifluoroacetic acid and triethylsilane to expose the thiols in preparation for further polymerisation. The resulting polymers (P10, P15, P21, P25, and P51, generated using different molar ratios) were reduced after 1.5 h of reduction time. Scanning electron microscopy images of the polymers showed spherical, loose, or tight patterns depending on the molar ratio of polymerisation. These polymers also exhibited efficient dissolution under various gastrointestinal conditions. Of the five polymers tested, P10 and P15 appeared to be promising drug delivery vehicles for poorly soluble drugs, due to the hydrophobic nature of the polymers.
    Matched MeSH terms: Amides
  2. Fulltext Synthesis of New Star-Shaped Liquid Crystalline Cyclotriphosphazene Derivatives with Fire Retardancy Bearing Amide-Azo and Azo-Azo Linking Units
    Jamain Z, Khairuddean M, Guan-Seng T
    Int J Mol Sci, 2020 Jun 16;21(12).
    PMID: 32560033 DOI: 10.3390/ijms21124267
    Two series of new hexasubstituted cyclotriphosphazene derivatives were successfully synthesized and characterized. These derivatives are differentiated by two types of linking units in the molecules such as amide-azo (6a-j) and azo-azo (8a-j). The homologues of the same series contain different terminal substituents such as heptyl, nonyl, decyl, dodecyl, tetradecyl, hydroxyl, carboxyl, chloro, nitro, and amino groups. All the intermediates and final compounds were characterized using Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (NMR), and Carbon, Hydrogen, and Nitrogen (CHN) elemental analysis. Liquid crystal properties for all compounds were determined using polarized optical microscope (POM). It was found that only intermediates 2a-e with nitro and alkoxyl terminal chains showed a smectic A phase. All the final compounds with alkoxyl substituents are mesogenic with either smectic A or C phases. However, other intermediates and compounds were found to be non-mesogenic. The study on the fire retardancy of final compounds was determined using limiting oxygen index (LOI) method. The LOI value of pure polyester resin (22.53%) was increased up to 24.71% after treating with 1 wt% of hexachlorocyclotriphosphazene (HCCP). Moreover, all the compounds gave positive results on the LOI values and compound 6i with the nitro terminal substituent showed the highest LOI value of 27.54%.
    Matched MeSH terms: Amides
  3. Fulltext Capsaicin: current understanding in therapeutic effects, drug interaction, and bioavailability
    Suk Huei Chan, Azrina Azlan, Amin Ismail, Nurul Husna Shafie
    Malaysian Journal of Medicine and Health Sciences, 2020;16(106):219-227.
    MyJurnal
    Capsaicin (N-vanillyl-8-methyl-6-(E)-none amide) is a unique and significant compound from group component of capsaicinoids. This component can only be found in the plants from the Capsicum genus. It is the primary source of pungency or spiciness of chilli pepper. Traditionally, capsaicin has been used to alleviate pain. Recently, some studies showed significant therapeutic effects of capsaicin in many diseases such as diabetes, hypertension, cancer and obesity. Determination of the most effective dosage used and underlying working mechanism of capsaicin are still in progress. Currently, capsaicin research, especially in drug interaction and encapsulation technologies, has not been reviewed. We aim to report current experimental evidence of capsaicin research focusing on its pharmacolog- ical properties, interaction with drugs and ways to improve the bioavailability of capsaicin. It is essential to provide a general orientation for further investigation that can discover more potency of capsaicin usage as a medicinal supplement to treat various diseases.
    Matched MeSH terms: Amides
  4. Fulltext Randomized Clinical Trial of Periarticular Drug Injectionused in combination Patient-Controlled Analgesia versusPatient-Controlled Analgesia Alone in Total KneeArthroplasty
    Sabran, M.N., Talha, A.J.M., Omar, M., Ibrahim, M.Y., Shahril, Y.
    Malays Orthop J, 2008;2(2):21-26.
    MyJurnal
    This is a prospective randomized clinical trial to compare use of a combination of periarticular drug injection with patientcontrolled analgesia (PCA) to PCA alone in post-total knee arthroplasty (TKA). Thirty patients who were admitted for unilateral total knee arthroplasty were selected randomly into an Injection group or a Standard group. The periarticular injection contained Ropivacaine, Ketorolac and Adrenaline, given intra-operatively. The mean amount of opioid used was 22.87 mmol/L in the Injection group as compared to 39.78 mmol/L in the Standard group (p = 0.026). The Injection group had lower pain score at rest and during exercise (p=0.021, p=0.041, respectively), as well as better return to function (p=0.026) and shorter hospital stay (6.1 days, Injection; 7.5 days, Standard, p=0.027). Overall, the group receiving periarticular drugs injection had less pain, less narcotic usage, earlier return to function, similar experience of adverse effects and shorter hospital stays.
    Matched MeSH terms: Amides
  5. Fulltext Mechanism of biosorption of Pb (ii) and Cu (ii) ions using dead biomass of Fusarium equiseti strain UMAS and Penicillium citrinum strain UMAS B2
    Wahab Abideen Akinkunmi, Awang Ahmad Sallehin Awang Husaini, Azham Zulkharnain, Tay, Meng Guan, Hairul Azman Roslan
    Journal of Biochemistry, Microbiology and Biotechnology, 2016;4(2):1-6.
    MyJurnal
    Filamentous fungi such as Fusarium equiseti KR706303 and Penicillium citrinum KR706304
    are capable of sequestering heavy metals from aqueous solutions. In the present study, the role
    play by various functional groups present in the cell wall of F. equiseti KR706303 and P.
    citrinum KR706304 during lead and copper ions biosorption was investigated. The fungal
    biomass was chemically treated to modify the functional groups present in their cell wall. These
    modifications were studied through biosorption experiments. It was found that an esterification
    of the carboxyl and phosphate groups, methylation of the amine groups and extraction of lipids
    significantly decrease the biosorption of both lead and copper ions studied. Therefore, the
    carbonyl, hydroxyl and amide groups were recognized as important in the biosorption of metal
    ions by the tested fungi. The study showed that there was no release of any metal ions from the
    biomass after biosorption, indicating that ion exchange may not be a key mechanism in the
    biosorption of lead and copper ions by these fungi but complexation of metal ions within the
    fungal cell wall.
    Matched MeSH terms: Amides
  6. Fulltext Isolation and characterization of a metal-reducing Pseudomonas sp. strain 135 with amide-degrading capability
    Yakasai, M.H., Rahman, M.F., Khayat, M.E., Shukor, M.Y., Shamaan, N.A., Rahim, M.B.H.A.
    Bioremediation Science and Technology Research, 2017;5(2):32-38.
    MyJurnal
    The presence of both heavy metals and organic xenobiotic pollutants in a contaminated site
    justifies the application of either a multitude of microbial degraders or microorganisms having
    the capacity to detoxify a number of pollutants at the same time. Molybdenum is an essential
    heavy metal that is toxic to ruminants at a high level. Ruminants such as cow and goats
    experience severe hypocuprosis leading to scouring and death at a concentration as low as
    several parts per million. In this study, a molybdenum-reducing bacterium with amide-degrading
    capacity has been isolated from contaminated soils. The bacterium, using glucose as the best
    electron donor reduces molybdenum in the form of sodium molybdate to molybdenum blue. The
    maximal pH reduction occurs between 6.0 and 6.3, and the bacterium showed an excellent
    reduction in temperatures between 25 and 40 oC. The reduction was maximal at molybdate
    concentrations of between 15 and 25 mM. Molybdenum reduction incidentally was inhibited by
    several toxic heavy metals. Other carbon sources including toxic xenobiotics such as amides
    were screened for their ability to support molybdate reduction. Of all the amides, only
    acrylamide can support molybdenum reduction. The other amides; such as acetamide and
    propionamide can support growth. Analysis using phylogenetic analysis resulted in a tentative
    identification of the bacterium as Pseudomonas sp. strain 135. This bacterium is essential in
    remediating sites contaminated with molybdenum, especially in agricultural soil co-contaminated
    with acrylamide, a known soil stabilizer.
    Matched MeSH terms: Acetamides; Amides
  7. Fulltext Pharmacophore modelling of vanillin derivatives, favipiravir, chloroquine, hydroxychloroquine, monolaurin and tetrodotoxin as MPro inhibitors of severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2)
    Law WY, Asaruddin MR, Bhawani SA, Mohamad S
    BMC Res Notes, 2020 Nov 11;13(1):527.
    PMID: 33176880 DOI: 10.1186/s13104-020-05379-6
    OBJECTIVES: The aim of this study was to use Ligand-based pharmacophore modelling approach for four established antiviral drugs, namely remdesivir, lopinavir, ritonavir and hydroxychloroquine for COVID-19 inhibitors as training sets. In this study Twenty vanillin derivatives together with monolaurin and tetrodotoxin were used as test sets to evaluate as potential SARS-CoV-2 inhibitors. The Structure-based pharmacophore modelling approach was also performed using 5RE6, 5REX and 5RFZ in order to analyse the binding site and ligand-protein complex interactions.

    RESULTS: The pharmacophore modelling mode of 5RE6 displayed two Hydrogen Bond Acceptors (HBA) and one Hydrophobic (HY) interaction. Besides, the pharmacophore model of 5REX showed two HBA and two HY interactions. Finally, the pharmacophore model of 5RFZ showed three HBA and one HY interaction. Based on ligand-based approach, 20 Schiff-based vanillin derivatives, showed strong MPro inhibition activity. This was due to their good alignment and common features to PDB-5RE6. Similarly, monolaurin and tetrodotoxin displayed some significant activity against SARS-CoV-2. From structure-based approach, vanillin derivatives (1) to (12) displayed some potent MPro inhibition against SARS-CoV-2. Favipiravir, chloroquine and hydroxychloroquine also showed some significant MPro inhibition.

    Matched MeSH terms: Amides/pharmacology; Amides/chemistry
  8. Pro-apoptotic carboxamide analogues of natural fislatifolic acid targeting Mcl-1 and Bcl-2
    Gapil Tiamas S, Daressy F, Abou Samra A, Bignon J, Steinmetz V, Litaudon M, et al.
    Bioorg Med Chem Lett, 2020 04 01;30(7):127003.
    PMID: 32035700 DOI: 10.1016/j.bmcl.2020.127003
    A library of 26 novel carboxamides deriving from natural fislatifolic acid has been prepared. The synthetic strategy involved a bio-inspired Diels-Alder cycloaddition, followed by functionalisations of the carbonyl moiety. All the compounds were evaluated on Bcl-xL, Mcl-1 and Bcl-2 proteins. In this series of cyclohexenyl chalcone analogues, six compounds behaved as dual Bcl-xL/Mcl-1 inhibitors in micromolar range and one exhibited sub-micromolar affinities toward Mcl-1 and Bcl-2. The most potent compounds evaluated on A549 and MCF7 cancer cell lines showed moderate cytotoxicities.
    Matched MeSH terms: Amides/chemical synthesis; Amides/pharmacology*
  9. Fulltext Comparing the effectiveness of ropivacaine 0.5% versus ropivacaine 0.2% for transabdominis plane block in providing postoperative analgesia after appendectomy
    Abdul Jalil RM, Yahya N, Sulaiman O, Wan Mat WR, Teo R, Izaham A, et al.
    Acta Anaesthesiol Taiwan, 2014 Jun;52(2):49-53.
    PMID: 25016507 DOI: 10.1016/j.aat.2014.05.007
    The basis for the transversus abdominis plane (TAP) block involves infiltration of a local anesthetic into the neurofascial plane between the internal oblique and the transversus abdominis muscles, causing a regional block that spreads between the L1 and T10 dermatomes. Thus, the TAP block is said to be suitable for lower abdominal surgery. This study was designed to compare the analgesic efficacy of two different concentrations of ropivacaine for TAP block in patients undergoing appendectomy.
    Matched MeSH terms: Amides/administration & dosage*
  10. Fulltext Cyclization vs. cyclization/dimerization in o-amidostilbene radical cation cascade reactions: the amide question
    Kee CH, Ariffin A, Awang K, Noorbatcha I, Takeya K, Morita H, et al.
    Molecules, 2011 Aug 25;16(9):7267-87.
    PMID: 21869754 DOI: 10.3390/molecules16097267
    The n-butyramido, isobutyramido, benzamido, and furancarboxamido functions profoundly modulate the electronics of the stilbene olefinic and NH groups and the corresponding radical cations in ways that influence the efficiency of the cyclization due presumably to conformational and stereoelectronic factors. For example, isobutyramido- stilbene undergoes FeCl(3) promoted cyclization to produce only indoline, while n-butyramidostilbene, under the same conditions, produces both indoline and bisindoline.
    Matched MeSH terms: Amides/chemistry*
  11. Challenges associated with the synthesis of unusual o-carboxamido stilbenes by the Heck protocol: Intriguing substituent effects, their toxicological and chemopreventive implications
    Kee CH, Ariffin A, Awang K, Takeya K, Morita H, Hussain SI, et al.
    Org Biomol Chem, 2010 Dec 21;8(24):5646-60.
    PMID: 20941451 DOI: 10.1039/c0ob00296h
    The syntheses of fourteen unusual o-carboxamido stilbenes by the Heck protocol revealed surprising complexity related to intriguing substituent effects with mechanistic implications. The unexpected cytotoxic and chemopreventive properties also seem to be substituent dependent. For example, although stilbene 15d (with a 4-methoxy substituent) showed cytotoxicity on HT29 colon cancer cells with an IC(50) of 4.9 μM, the 3,4-dimethoxy derivative (15c) is inactive. It is interesting to observe that the 3,5-dimethoxy derivative (15e) showed remarkable chemopreventive activity in WRL-68 fetal hepatocytes, surpassing the gold standard, resveratrol. The resveratrol concentration needed to be 5 times higher than that of 15e to produce comparable elevation of NQO1.
    Matched MeSH terms: Amides/chemistry*
  12. Antioxidant, anti-TB activities, phenolic and amide contents of standardised extracts of Piper sarmentosum Roxb
    Hussain K, Ismail Z, Sadikun A, Ibrahim P
    Nat Prod Res, 2009;23(3):238-49.
    PMID: 19235024 DOI: 10.1080/14786410801987597
    Ethanol and aqueous extracts of the different parts of Piper sarmentosum were analysed by HPLC for marker compounds to standardise these extracts. The standardised extracts were investigated for antioxidant activity (beta-carotene linoleate model and DPPH model), anti-TB activity (microplate tetrazolium assay), and estimation of total phenolic and amide contents. The extracts of the different parts exhibited different antioxidant activity, phenolic and amide contents (p < 0.01). The ethanol extracts exhibited better antioxidant activity as compared to the aqueous extracts. The leaf ethanol extract was further investigated for dose response relationship and its EC(50) was found to be 38 microg mL(-1). All the extracts have exhibited anti-TB activity with MIC/MBC 12.5 microg mL(-1). The leaf methanol extract was fractionated and the ethyl acetate fraction exhibited anti-TB activity with MIC/MBC 3.12 microg mL(-1) while MIC/MBC of isoniazid (INH) was found to be 0.5 microg mL(-1). A positive correlation was found between antioxidant activity and total polyphenols, flavonoids and amides, in the beta-carotene linoleate model (p = 0.05) and in the DPPH model (p = 0.01). The analytical method was found to have linearity >0.9922, coefficient of variance <5% and accuracy 95.5 +/- 5 to 96.9 +/- 5. This plant possesses promising antioxidant as well as anti-TB properties.
    Matched MeSH terms: Amides/chemistry*
  13. Fulltext Preemptive ropivacaine local anaesthetic infiltration versus postoperative ropivacaine wound infiltration in mastectomy: postoperative pain and drain outputs
    Rica MA, Norlia A, Rohaizak M, Naqiyah I
    Asian J Surg, 2007 Jan;30(1):34-9.
    PMID: 17337369
    OBJECTIVE: The aim of this study was to investigate if preemptive local infiltration (PLA) with ropivacaine could improve postoperative pain and determine its effect on drain output postmastectomy with axillary dissection.
    METHODS: This was a prospective, randomized trial comprising 30 women allocated to two groups: one to receive postoperative wound infiltration (POW) of 20 mL of 0.2% (40 mg) ropivacaine (Naropin) versus PLA with 20 mL of 0.2% ropivacaine (Naropin) diluted with 80 mL of 0.9% saline, total volume 100 mL. A visual analogue scale (0-100 mm) and angle of shoulder abduction were used for evaluation of pain. Postoperatively, all patients received oral ibuprofen 400 mg tds.
    RESULTS: There was no significant difference in postoperative pain for the first 3 days between the two groups. There were wider shoulder abduction angles in the 1st and 3rd postoperative days in the PLA group, but this was not significant. Operative time was significantly shorter in the PLA group than in the POW group (69.34+/-59.37 minutes vs. 109.67+/-26.96 minutes; p=0.02). The axillary drain was removed earlier in the preemptive group, 5.4+/-1.55 days versus 6.8+/-2.04 days in the postoperative group (p=0.04).
    CONCLUSION: We found no difference in postoperative pain between preemptive tumescent ropivacaine infiltration and postoperative ropivacaine wound infiltration.
    Matched MeSH terms: Amides/administration & dosage*
  14. Alkyl amides and nitriles as novel tracers for biomass burning
    Rushdi AI, bin Abas MR, Didyk BM
    Environ Sci Technol, 2003 Jan 1;37(1):16-21.
    PMID: 12542285
    The occurrence of n-alkanoic acids, amides, and nitriles in samples of aerosol particulate matter from Kuala Lumpur and Santiago suggests that emissions from cooking and biomass burning are the primary sources of these organic markers in the atmosphere. It is proposed that fatty acids react with ammonia during biomass burning or combustion to produce amides and nitriles, which can be applied as useful biomarker tracers. To test this hypothesis, nonadecanoic acid and hexadecanamide were used as reactants in hydrous pyrolysis experiments. These experiments produced amides and nitriles and indicated that ammonia is an essential agent in their formation. Thus amides and nitriles are of utility as indicators for input from combustion and biomass burning in the ambient atmosphere.
    Matched MeSH terms: Amides/analysis*
  15. Discovery of azetidine based ene-amides as potent bacterial enoyl ACP reductase (FabI) inhibitors
    Takhi M, Sreenivas K, Reddy CK, Munikumar M, Praveena K, Sudheer P, et al.
    Eur J Med Chem, 2014 Sep 12;84:382-94.
    PMID: 25036796 DOI: 10.1016/j.ejmech.2014.07.036
    A novel and potent series of ene-amides featuring azetidines has been developed as FabI inhibitors active against drug resistant Gram-positive pathogens particularly staphylococcal organisms. Most of the compounds from the series possessed excellent biochemical inhibition of Staphylococcus aureus FabI enzyme and whole cell activity against clinically relevant MRSA, MSSA and MRSE organisms which are responsible for significant morbidity and mortality in community as well as hospital settings. The binding mode of one of the leads, AEA16, in Escherichia coli FabI enzyme was determined unambiguously using X-ray crystallography. The lead compounds displayed good metabolic stability in mice liver microsomes and pharmacokinetic profile in mice. The in vivo efficacy of lead AEA16 has been demonstrated in a lethal murine systemic infection model.
    Matched MeSH terms: Amides/metabolism; Amides/pharmacology*; Amides/chemistry
  16. Fulltext Holistic approach to microwave-reflux extraction and thermo-analytical fingerprints of under-utilized Artocarpus heterophyllus seed wastes
    Olalere OA, Gan CY, Abdurahman HN, Adeyi O, Ahmad MM
    Heliyon, 2020 Aug;6(8):e04770.
    PMID: 32923719 DOI: 10.1016/j.heliyon.2020.e04770
    The increase in wastes generated from jackfruit seeds has been largely under-utilized in Malaysia. Due to the high nutritional and medicinal content embedded in the cellulosic structure of jackfruit wastes, a need then arises for their physicochemical elucidations. In this study, the extraction of Artocarpus heterophyllus seed was carefully investigated using Taguchi orthogonal optimization design. Complete functional group characteristics and chemical profile of the A. heterophyllus seed extracts were obtained using different physicochemical characterization. The optimal conditions of the microwave extraction parameters were determined at 5 min of irradiation time, 450 W of power and 50 °C of temperature. Under this condition, the optimal yield of 17.34 (mg/g) % was achieved at an SNR ratio of 24.78. The mass spectrometry analysis tentatively identified a total of 90 and 148 secondary metabolites at positive and negative ESI modes, respectively. The chemical profile obtained provided a baseline reference for further investigation on the food and medicinal bioactive from Artocarpus heterophyllus seed oleoresins. The FT-infrared emission spectrum shows the presence of some specific carbohydrates and amide protein functional groups directly linked to C-O (1008 cm-1) the carbonyl (C=O) groups, respectively. Moreover, the morphological characteristics of the jackfruit raw and crude extracts conspicuously revealed large-sized globules which suggest the carbohydrates and protein contents. The result of this study indicates that the use of microwave extraction technology produced high-quality extracts with lower degradation of the thermal labile constituents. This will assist in determining the suitable conditions necessary for the total recovery of medicinal and nutritional constituents and conversion of agricultural waste products into useful products.
    Matched MeSH terms: Amides
  17. Fulltext Effect of different types of hydrocolloids on the physical and sensory properties of ice cream with fermented glutinous rice ( tapai pulut)
    Shukri, W.H.Z., Hamzah, E.N.H., Halim, N.R.A., Isa, M.I.N., Sarbon, N.M.
    International Food Research Journal, 2014;21(5):1777-1787.
    MyJurnal
    The aim of this work is to study the effect of hydrocolloids (guar gum, xanthan gum and carboxymethyl cellulose (CMC) on the physical properties and sensory evaluation of ice cream produced in order to investigate the potential of applying fermented glutinous rice (tapai pulut) as a value-added ingredient. The addition of 25% fermented glutinous rice was the most reliable amount to enhance the physical and sensory properties of ice cream when incorporating hydrocolloids. The addition of hydrocolloids significantly (p < 0.05) increased the pH, firmness, overrun, and melting rate of fermented glutinous rice ice cream. The addition of guar gum scored the highest firmness value (5403 g) followed by CMC (4630 g) and xanthan gum (3481g). Fermented glutinous rice ice cream with xanthan gum added, induced a noticeable change in overrun value (62%) while the addition of CMC decreased the melting rate compared to the control. The FTIR spectrum of fermented glutinous rice ice cream with different hydrocolloids containing carboxyl, amide and carbonyl group was appeared at 3362-3379 cm-1 , 1639-1640 cm-1 and 1026-1064 cm-1, respectively. In conclusion, the addition of xanthan gum presented great potential to improve the quality of fermented glutinous rice ice cream produced in terms of its firmness, overrun and melting rate.
    Matched MeSH terms: Amides
  18. Mechanical and thermal properties of palm-based polyurethane composites filled with Fe3O4, PANI and PANI/Fe3O4
    Liow CH, Sahrim Ahmad, Khairiah Badri
    Sains Malaysiana, 2011;40.
    In-situ polymerization method was used to prepare palm-based polyurethane (PU) composites loading with 15 wt% magnetite (Fe3O4), polyaniline (PANI) and Fe3O4 coated with PANI labeled as PU15, PP and PPM, respectively. FTIR spectroscopy analysis indicated a shift in the carbonyl, C=O and NH in PP. The shift of the peak indicated that there was hydrogen bonding between the C=O (proton acceptor) of urethane with NH (proton-donator) of PANI. PPM gave the highest impact and flexural strengths at 4875 kJ/ m2 and 42 MPa, respectively but with the lowest flexural modulus (1050 MPa). Two-stage degradation behavior was observed in the TGA thermogram.
    Matched MeSH terms: Amides
  19. Experimental and DFT investigation on the influence of electron donour/acceptor on the hydrogen bonding interactions of 1-(1,3-benzothiazol-2-yl)-3-(r-benzoylthiourea)
    Wun FML, Muhd Hafizi Zainal, Syahidah Mohd Tahir, Ishak B. Ahmad, Mohammad B. Kassim
    Sains Malaysiana, 2018;47:923-929.
    The presence of two different chromophores in benzothiazole molecule namely benzothiazole and aromatic rings lead to
    interesting chemical and biological properties that attract more researches on the compounds. Three new benzothiazolylbenzoythiourea
    compounds namely 1-(1,3-benzothiazol-2-yl)-3-(benzoylthiourea) (BBT), 1-(1,3-benzothiazol-2-yl)-3-
    (4-chlorobenzoylthiourea) (BBT-4Cl) and 1-(1,3-benzothiazol-2-yl)-3-(4-methoxybenzoylthiourea) (BBT-4OCH3
    ) with
    different electron withdrawing substituents (R) at the para positions on the benzene ring of benzoylthiourea ring have
    been synthesized from the reaction of R-benzoyl isothiocyanate (R= H, Cl, and OCH3
    ) and 2-aminobenzothiazole. The
    compounds were characterized by spectroscopic techniques (infrared, 1
    H proton NMR and UV-Vis). The IR spectra showed
    the frequency signals of n (C=O), n (C=S), n (N-H) at 1664-1673, 1238-1249 and 3031-3055 cm-1, respectively. The 1
    H
    proton NMR spectra showed the presence of N-H amine and amide signals in the region of (12.14-12.35) and (14.17-14.43)
    ppm, respectively. The proton signals of the two benzothiazole and benzoylthiourea moieties appear at 7.08-8.16 ppm.
    A theoretical study based on Density Functional Theory (DFT) and Time-Dependent (TD) DFT was conducted to optimize
    the geometrical structure and investigate the electronic properties of title compounds. The highest occupied molecular
    orbital (HOMO) was found on the benzothiazole moiety; while, the lowest-unoccupied molecular orbital (LUMO) was
    located at the benzoylthiourea fragment. The DFT optimized structures possessed an intramolecular hydrogen bonding
    and the types of para substituents used influenced the properties of hydrogen bonding.
    Matched MeSH terms: Amides
  20. Fulltext Dexibuprofen amide derivatives as potential anticancer agents: synthesis, in silico docking, bioevaluation, and molecular dynamic simulation
    Ashraf Z, Mahmood T, Hassan M, Afzal S, Rafique H, Afzal K, et al.
    Drug Des Devel Ther, 2019;13:1643-1657.
    PMID: 31190743 DOI: 10.2147/DDDT.S178595
    BACKGROUND: The amide derivatives of nonsteroidal anti-inflammatory drugs have been reported to possess antitumor activity. The present work describes the synthesis of dexibuprofen amide analogues (4a-j) as potential anticancer agents.

    METHODS: The title amides (4a-j) were obtained by simple nucleophilic substitution reaction of dexibuprofen acid chloride with substituted amines in good yield and chemical structures were confirmed by FTIR, 1H NMR, 13C NMR and mass spectral data.

    RESULTS: The brine shrimp lethality assay results showed that all of the synthesized compounds are non-toxic to shrimp larvae. The inhibitory effects on tumor growth were evaluated and it was observed that N-(2,5-dichlorophenyl)-2-(4-isobutylphenyl) propionamide (4e) and N-(2-chlorophenyl)-2-(4-isobutylphenyl) propionamide (4g) exhibited excellent antitumor activity compared to all other derivatives. The compound 4e bearing 2,5-dichloro substituted phenyl ring and 4g possesses 2-chloro substituted phenyl ring exhibited 100% inhibition of the tumor growth. The anticancer activity was evaluated against breast carcinoma cell line (MCF-7) and it was observed that derivative 4e exhibited excellent growth inhibition of cancer cells with IC50 value of 0.01±0.002 µm, which is better than the standard drugs. The docking studies against breast cancer type 1 susceptibility protein BRCA1 (PDBID 3K0H) exhibited good binding affinities, which are in good agreement with the wet lab results. The compounds 4e and 4g showed the binding energy values of -6.39 and -6.34 Kcal/mol, respectively. The molecular dynamic (MD) simulation was also carried out to evaluate the residual flexibility of the best docking complexes of compounds 4e and 4g. The MD simulation analysis assured that the 4e formed a more stable complex with the target protein than the 4g. The synthesized amide derivatives exhibited were devoid of gastrointestinal side effects and no cytotoxic effects against human normal epithelial breast cell line (MCF-12A) were found.

    CONCLUSION: Based upon our wet lab and dry lab findings we propose that dexibuprofen analogue 4e may serve as a lead structure for the design of more potent anticancer drugs.

    Matched MeSH terms: Amides/chemical synthesis; Amides/pharmacology*; Amides/chemistry
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