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Fulltext 3-(2-Amino-phenyl-sulfanyl)-1,3-diphenyl-propan-1-one

Yaeghoobi M, Khaledi H, Abdullah Z, Abd Rahman N

Acta Crystallogr Sect E Struct Rep Online, 2011 Jul 1;67(Pt 7):o1693.

PMID: 21837090 DOI: 10.1107/S1600536811022112

In the title compound, C(21)H(19)NOS, the three aromatic rings are not coplanar, the dihedral angles between them being 84.75 (7), 88.01 (8) and 8.36 (16)°. In the crystal, two types of C-H⋯ π inter-actions, one of which is weak, and N-H⋯π inter-actions link the mol-ecules into layers parallel to the ab plane.

Fulltext Synthesis, characterization, X-ray crystallography, acetyl cholinesterase inhibition and antioxidant activities of some novel ketone derivatives of gallic hydrazide-derived Schiff bases

Gwaram NS, Ali HM, Abdulla MA, Buckle MJ, Sukumaran SD, Chung LY, et al.

Molecules, 2012 Feb 28;17(3):2408-27.

PMID: 22374313 DOI: 10.3390/molecules17032408

Alzheimer's disease (AD) is the most common form of dementia among older people and the pathogenesis of this disease is associated with oxidative stress. Acetylcholinesterase inhibitors with antioxidant activities are considered potential treatments for AD. Some novel ketone derivatives of gallic hydrazide-derived Schiff bases were synthesized and examined for their antioxidant activities and in vitro and in silico acetyl cholinesterase inhibition. The compounds were characterized using spectroscopy and X-ray crystallography. The ferric reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays revealed that all the compounds have strong antioxidant activities. N-(1-(5-bromo-2-hydroxyphenyl)-ethylidene)-3,4,5-trihydroxybenzohydrazide (2) was the most potent inhibitor of human acetyl cholinesterase, giving an inhibition rate of 77% at 100 μM. Molecular docking simulation of the ligand-enzyme complex suggested that the ligand may be positioned in the enzyme's active-site gorge, interacting with residues in the peripheral anionic subsite (PAS) and acyl binding pocket (ABP). The current work warrants further preclinical studies to assess the potential for these novel compounds for the treatment of AD.

Heterometallic Pd(II)-Ni(II) complexes with meso-substituted dibenzotetraaza[14]annulene: double C-H bond activation and formation of a rectangular tetradibenzotetraaza[14]annulene

Khaledi H, Olmstead MM, Fukuda T, Ali HM

Inorg Chem, 2014 Nov 3;53(21):11348-50.

PMID: 25320842 DOI: 10.1021/ic5019828

Three isomeric 2[Pd(II)-Ni(II)] metal complexes, derived from indoleninyl meso-substituted dibenzotetraaza[14]annulene, were synthesized. The resulting dimers feature Ni···Ni or, alternatively, Ni···π interactions in staggered or slipped cofacial structures. A remarkable insertion of palladium into two different C-H bonds yielded a 4[Pd(II)-Ni(II)] rectangular complex with dimensions of 8.73 × 10.38 Å.

Fulltext Corrosion inhibition properties of pyrazolylindolenine compounds on copper surface in acidic media

Ebadi M, Basirun WJ, Khaledi H, Ali HM

Chem Cent J, 2012 Dec 31;6(1):163.

PMID: 23276247 DOI: 10.1186/1752-153X-6-163

BACKGROUND: The corrosion inhibition performance of pyrazolylindolenine compounds, namely 4-(3,3-dimethyl-3H-indol-2-yl)-pyrazole-1-carbothioamide (InPzTAm), 4-(3,3-dimethyl-3H-indol-2-yl)-1H-pyrazole-1-carbothiohydrazide (InPzTH) and 3,3-dimethyl-2-(1-phenyl-1H-pyrazol-4-yl)-3H-indole (InPzPh),) on copper in 1M HCl solution is investigated by electrochemical impedance spectroscopy (EIS), open circuit potential (OCP) and linear scan voltammetry (LSV) techniques.

RESULTS: The results show that the corrosion rate of copper is diminished by the compounds with the inhibition strength in the order of: InPzTAm> InPzTH > InPzPh. The corrosion inhibition efficiencies for the three inhibitors are 94.0, 91.4 and 79.3, for InPzTAm, InPzTH and InPzPh respectively with the same inhibitor concentration (2 mM).

CONCLUSION: From the EIS, OCP and LSV results it was concluded that pyrazolylindolenine compounds with S-atom (with an amine group) have illustrated better corrosion inhibition performance compared to hydrazine and phenyl group.

Fulltext Cytoprotective effect of benzyl N'-(5-chloro-indol-3-yl-methylidene)-hydrazinecarbodithioate against ethanol-induced gastric mucosal injury in rats

Hashim H, Mughrabi FF, Ameen M, Khaledi H, Ali HM

Molecules, 2012 Aug 03;17(8):9306-20.

PMID: 22864239 DOI: 10.3390/molecules17089306

Indolic compounds have attracted a lot of attention due to their interesting biological properties. The present study was performed to evaluate the subacute toxicity and anti-ulcer activity of BClHC against ethanol-induced gastric ulcers. Experimental animal groups were orally pre-treated with different doses of BClHC (50, 100, 200 and 400 mg/kg) in 10% Tween 20 solution (vehicle). Blank and ulcer control groups were pre-treated with vehicle. The positive group was orally pretreated with 20 mg/kg omeprazole. After one hour, all groups received absolute ethanol (5 mL/kg) to generate gastric mucosal injury except the blank control group which was administered the vehicle solution. After an additional hour, all rats were sacrificed, and the ulcer areas of the gastric walls determined. Grossly, the ulcer control group exhibited severe mucosal injury, whereas pre-treatment with either derivative or omeprazole resulted in significant protection of gastric mucosal injury. Flattening of gastric mucosal folds was also observed in rats pretreated with BClHC. Histological studies of the gastric wall of ulcer control group revealed severe damage of gastric mucosa, along with edema and leucocytes infiltration of the submucosal layer compared to rats pre-treated with either BClHC or omeprazole where there were marked gastric protection along with reduction or absence of edema and leucocytes infiltration of the submucosal layer. Subacute toxicity study with a higher dose of derivative (5 g/kg) did not manifest any toxicological signs in rats. In conclusions, the present finding suggests that benzyl N'-(5-chloroindol-3-ylmethylidene)hydrazinecarbodithioate promotes ulcer protection as ascertained by the comparative decreases in ulcer areas, reduction of edema and leucocytes infiltration of the submucosal layer.

Fulltext Butylated hydroxytoluene analogs: synthesis and evaluation of their multipotent antioxidant activities

Yehye WA, Abdul Rahman N, Alhadi AA, Khaledi H, Weng NS, Ariffin A

Molecules, 2012 Jun 25;17(7):7645-65.

PMID: 22732881 DOI: 10.3390/molecules17077645

A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by the PASS program. Compounds 3 and 5 showed more inhibition of DPPH stable free radical at 10⁻⁴ M than the well-known standard antioxidant, butylated hydroxytoluene (BHT). Compound 5 exhibited promising in vitro inhibition of Fe²⁺-induced lipid peroxidation of the essential egg yolk as a lipid-rich medium (83.99%, IC₅₀ 16.07 ± 3.51 μM/mL) compared to α-tocopherol (α-TOH, 84.6%, IC₅₀ 5.6 ± 1.09 μM/mL). The parameters for drug-likeness of these BHT analogues were also evaluated according to the Lipinski’s “rule-of-five” (RO5). All the BHT analogues were found to violate one of the Lipinski’s parameters (LogP > 5), even though they have been found to be soluble in protic solvents. The predictive polar surface area (PSA) and absorption percent (% ABS) data allow us to conclude that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these new multipotent antioxidants (MPAOs) as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.

A new chromanone acid from the stem bark of Calophyllum teysmannii

Lim CK, Subramaniam H, Say YH, Jong VY, Khaledi H, Chee CF

Nat Prod Res, 2015;29(21):1970-7.

PMID: 25716662 DOI: 10.1080/14786419.2015.1015020

A new chromanone acid, namely caloteysmannic acid (1), along with three known compounds, calolongic acid (2), isocalolongic acid (3) and stigmasterol (4) were isolated from the stem bark of Calophyllum teysmannii. All these compounds were evaluated for their cytotoxic and antioxidant activities in the MTT and DPPH assays, respectively. The structure of compound 1 was determined by means of spectroscopic methods including 1D and 2D NMR experiments as well as HR-EIMS spectrometry. The stereochemical assignment of compound 1 was done based on the NMR results and X-ray crystallographic analysis. The preliminary assay results revealed that all the test compounds displayed potent inhibitory activity against HeLa cancer cell line, in particular with compound 1 which exhibited the highest cytotoxic activity comparable to the positive control used, cisplatin. However, no significant antioxidant activity was observed for all the test compounds in the DPPH radical scavenging capacity assay.

Antioxidant, cytotoxic activities, and structure-activity relationship of gallic acid-based indole derivatives

Khaledi H, Alhadi AA, Yehye WA, Ali HM, Abdulla MA, Hassandarvish P

Arch Pharm (Weinheim), 2011 Nov;344(11):703-9.

PMID: 21953995 DOI: 10.1002/ardp.201000223

A new series of gallic hydrazones containing an indole moiety was synthesized through the reaction of gallic hydrazide and different indole carboxaldehydes. Their antioxidant activities were determined on DPPH radical scavenging and inhibition of lipid peroxidation. The in-vitro cytotoxic activities of the compounds were evaluated against HCT-116 (human colon cancer cell line) and MCF-7 (estrogen-dependent human breast cancer cell line) by the MTT method. An attempt to correlate the biological results with their structural characteristics has been done. A limited positive structure activity relationship was found between cytotoxic and antioxidant activities.

Effect of bis [benzyl N'-(indol-3-ylmethylene)-hydrazinecarbodithioato]-zinc(II) derivatives on wound healing in Sprague Dawley rats

Mughrabi FF, Hashim H, Ameen M, Khaledi H, Ali HM, Ismail S

Indian J Exp Biol, 2011 Jan;49(1):50-5.

PMID: 21365996

Effects of topical application of Bis[benzyl N'-(indol-3-ylmethylene)-hydrazinecarbodithioato]-zinc(II) (BHCZ) on wound healing and histology of healed wound were assessed. Sprague Dawley rats were experimentally induced wound in the posterior neck area. Tween 20 (0.2 ml of 10%) was applied to rats in Group 1 (negative control). Intrasite gel (0.2 ml) was applied topically to rats in Group 2 as reference. BHCZ at the concentrations 0.2 ml of 25, 50 and 100 mg/ml were applied to Group 3, 4 and 5, respectively. Wound dressed with BHCZ significantly healed earlier than those treated with 10% Tween 20. Also wound dressed with 100 mg/ml BHCZ accelerated the rate of wound healing compared to those dressed with intrasite gel and, 25 mg/ml and 50 mg/ml BHCZ. Histological analysis of healed wound with BHCZ showed comparatively less scar width at wound enclosure and the healed wound contained less macrophages and large amount of collagen with angiogenesis compared to wounds dressed with 10% Tween 20. Results of this study showed that wounds dressed with 100 mg/ml of BHCZ significantly enhanced acceleration of the rate of wound healing enclosure, and histology of healed wounds showed comparatively less macrophages and more collagen with angiogenesis.

Indole-7-carbaldehyde thiosemicarbazone as a flexidentate ligand toward ZnII, CdII, PdII and PtII ions: cytotoxic and apoptosis-inducing properties of the PtII complex

Ibrahim AA, Khaledi H, Hassandarvish P, Mohd Ali H, Karimian H

Dalton Trans, 2014 Mar 14;43(10):3850-60.

PMID: 24442181 DOI: 10.1039/c3dt53032a

A new thiosemicarbazone (LH2) derived from indole-7-carbaldehyde was synthesized and reacted with Zn(II), Cd(II), Pd(II) and Pt(II) salts. The reactions with zinc and cadmium salts in 2 : 1 (ligand-metal) molar ratio afforded complexes of the type MX2(LH2)2, (X = Cl, Br or OAc), in which the thiosemicarbazone acts as a neutral S-monodentate ligand. In the presence of potassium hydroxide, the reaction of LH2 with ZnBr2 resulted in deprotonation of the thiosemicarbazone at the hydrazine and indole nitrogens to form Zn(L)(CH3OH). The reaction of LH2 with K2PdCl4 in the presence of triethylamine, afforded Pd(L)(LH2) which contains two thiosemicarbazone ligands: one being dianionic N,N,S-tridentate while the other one is neutral S-monodentate. When PdCl2(PPh3)2 was used as the Pd(II) ion source, Pd(L)(PPh3) was obtained. In a similar manner, the analogous platinum complex, Pt(L)(PPh3), was synthesized. The thiosemicarbazone in the latter two complexes behaves in a dianionic N,N,S-tridentate fashion. The platinum complex was found to have significant cytotoxicity toward four cancer cells lines, namely MDA-MB-231, MCF-7, HT-29, and HCT-116 but not toward the normal liver WRL-68 cell line. The apoptosis-inducing properties of the Pt complex was explored through fluorescence microscopy visualization, DNA fragmentation analysis and propidium iodide flow cytometry.

Fulltext tert-Butyl 2-(1H-benzimidazol-1-yl)acetate

N Al-Mohammed N, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2012 Mar 1;68(Pt 3):o571.

PMID: 22412488 DOI: 10.1107/S1600536812002814

In the title compound, C(13)H(16)N(2)O(2), the planes of the benzimidazole ring system and the acetate O-C=O fragment make a dihedral angle of 84.5 (3)°. In the crystal, mol-ecules are connected through C-H⋯N hydrogen bonds to form infinite chains in the [-110] direction.

Fulltext N,N'-{[Ethane-1,2-diylbis(-oxy)]bis-(ethane-2,1-di-yl)}bis-(4-methyl-benzene-sulfonamide)

Al-Mohammed NN, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2012 Jul 1;68(Pt 7):o1983.

PMID: 22807816 DOI: 10.1107/S1600536812024324

The asymmetric unit of the title compound, C(20)H(28)N(2)O(6)S(2), contains one half-mol-ecule, related to the other half by a twofold rotation axis. The two aromatic rings of the mol-ecule make a dihedral angle of 50.91 (7)°. The O-CH(2)-CH(2)-O and N-CH(2)-CH(2)-O fragments both adopt gauche conformations, with torsion angles of 76.0 (4) and 70.4 (3)°, respectively. In the crystal, adjacent mol-ecules are linked through N-H⋯O hydrogen bonds into chains along the a-axis direction. The chains are further connected via C-H⋯O inter-actions into a two-dimensional supra-molecular network in the ac plane.

Fulltext tert-Butyl 2-(1H-imidazol-1-yl)acetate

Al-Mohammed NN, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2012 Feb 1;68(Pt 2):o445.

PMID: 22347056 DOI: 10.1107/S1600536812001067

In the title compound, C(9)H(14)N(2)O(2), the imidazole ring and the acetate O-C=O plane make a dihedral angle of 80.54 (12)°. In the crystal, mol-ecules are connected via pairs of C-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Fulltext 1-Carb-oxy-methyl-3-octylimidazolium bromide

N Al-Mohammed N, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2011 Jul 1;67(Pt 7):o1701.

PMID: 21837097 DOI: 10.1107/S1600536811022094

In the title compound, C(13)H(23)N(2)O(2) (+)·Br(-), the octyl chain has an all-trans conformation. In the crystal, the cations are linked by C-H⋯O bonds into a zigzag chain along the b axis. The bromide anions further link the chains via C-H⋯Br inter-actions into a two-dimensional array parallel to the ab plane. An O-H⋯Br interaction is also observed.

Fulltext Imidazo[1,2-b]isoquinoline-5,10-dione

N Al-Mohammed N, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2011 Jul 1;67(Pt 7):o1666.

PMID: 21837065 DOI: 10.1107/S1600536811022082

The title butterfly-shaped mol-ecule, C(11)H(6)N(2)O(2), is folded slightly along the O=C⋯C=O line, the dihedral angle between the two parts being 6.42 (3)°. In the crystal, adjacent mol-ecules are linked through C-H⋯O hydrogen bonds into infinite layers parallel to the ac plane. The layers are further connected into a three-dimensional netweork via π-π inter-actions formed between pairs of anti-parallel arranged mol-ecules, with a centroid-centroid distance between the central six-membered ring and the benzene ring of 3.4349 (9) Å.

Fulltext 1,1'-{[1,4-Phenyl-enebis(methyl-ene)]bis-(-oxy)bis-(4,1-phenyl-ene)}diethanone

Al-Mohammed NN, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2011 Dec 1;67(Pt 12):o3164.

PMID: 22199688 DOI: 10.1107/S160053681104565X

The centroid of the central aromatic ring of the title mol-ecule, C(24)H(22)O(4), is located on an inversion center. The dihedral angle between the central and terminal benzene rings is 75.00 (7)°. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds into chains along [121]. The chains are connected into layers via C-H⋯π inter-actions.

Fulltext 1,1'-{[1,4-Phenyl-enebis(methyl-ene)]bis-(-oxy)bis-(3,1-phenyl-ene)}diethanone

Al-Mohammed NN, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2011 Dec 1;67(Pt 12):o3140.

PMID: 22199668 DOI: 10.1107/S1600536811045041

In the title compound, C(24)H(22)O(4), the centroid of the central benzene ring lies on a special position of 2/m site symmetry, while the terminal aromatic rings are located on a mirror plane. The central and terminal benzene rings are perpendic-ular to each other. In the crystal, the mol-ecules are connected via C-H⋯O hydrogen bonds into a three-dimensional polymeric structure. The network is further consolidated by a C-H⋯π inter-action.

Fulltext 1-Tosyl-2-[(1-tosyl-1H-benzimidazol-2-yl)methyl-sulfanyl]-1H-benzimidazole

N Al-Mohammed N, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2011 May 1;67(Pt 5):o1043.

PMID: 21754370 DOI: 10.1107/S1600536811011822

In the title compound, C(29)H(24)N(4)O(4)S(3), the two N-tosyl-benzimidazolyl unit are connected through a -S-CH(2)- fragment, the dihedral angle between the benzimidazole rings being 76.09 (5)°. The methyl-thio group is disordered with respect to exchange of the S and C atoms in a 0.547 (4):0.453 (4) ratio. In the crystal, C-H⋯O and C-H⋯π inter-actions connect adjacent mol-ecules into infinite layers parallel to the ab plane. The crystal packing is further stabilized by a π-π inter-action [centroid-centroid separation = 3.5187 (4) Å].

Fulltext 4,4',6,6'-Tetra-tert-butyl-2,2'-[butane-1,4-diylbis(nitrilo-methanylyl-idene)]diphenol

Tee JT, Abdullah N, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2011 Nov;67(Pt 11):o2954.

PMID: 22219980 DOI: 10.1107/S1600536811041614

The title compound, C(34)H(52)N(2)O(2), is centrosymmetric, the mid-point of the central C-C bond being located on an inversion centre. Intra-molecular O-H⋯N and weak C-H⋯O hydrogen bonds are observed, but no significant inter-molecular inter-actions occur in the crystal structure.

Fulltext 1,1'-{2,2'-[1,4-Phenyl-enebis(methyl-ene)]bis-(-oxy)bis-(2,1-phenyl-ene)}diethanone

Al-Mohammed NN, Alias Y, Abdullah Z, Khaledi H

Acta Crystallogr Sect E Struct Rep Online, 2011 Nov;67(Pt 11):o3016.

PMID: 22220033 DOI: 10.1107/S1600536811042528

The asymmetric unit of the title compound, C(24)H(22)O(4), contains one half-mol-ecule, the other half being generated by a crystallographic center of inversion. The central benzene ring makes a dihedral angle of 72.49 (5)° with the terminal benzene ring. In the crystal, adjacent mol-ecules are linked through C-H⋯O inter-actions, forming a sheet structure parallel to the bc plane. The sheets are stacked along the a axis via π-π inter-actions formed between the terminal benzene rings [centroid-centroid separation = 3.7276 (6) Å].

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