MyMedR

Fulltext 2-{[2-(2-Hy-droxy-5-meth-oxy-benzyl-idene)hydrazin-1-yl-idene]meth-yl}-4-meth-oxy-phenol

Taha M, Shah SA, Sultan S, Ismail NH, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2014 Feb 01;70(Pt 2):o131.

PMID: 24764858 DOI: 10.1107/S1600536813034636

The title phenyl-hydrazine derivative, C16H16N2O4, has a crystallographically imposed centre of symmetry. Except for the methyl group, all non-H atoms are almost coplanar (r.m.s. deviation = 0.0095 Å). Intra-molecular O-H⋯N hydrogen bonds are observed, generating S(6) graph-set ring motifs.

Fulltext (E)-4-Meth-oxy-N'-(3,4,5-trihy-droxy-benzyl-idene)benzohydrazide methanol monosolvate

Taha M, Naz H, Rahman AA, Ismail NH, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2012 Oct 1;68(Pt 10):o2846.

PMID: 23125650 DOI: 10.1107/S1600536812036550

The title compound, C(15)H(14)N(2)O(5)·CH(3)OH, displays an E conformation about the azomethine double bond [C=N = 1.277 (2) Å] and the benzene rings are inclined to one another by 18.28 (9)°. An intra-molecular O-H⋯O hydrogen bond occurs between the para-OH group and one of the meta-O atoms of the 3,4,5-trihy-droxy-benzyl-idene group. In the crystal, the components are linked into a three dimensional network by O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds.

Fulltext Bis-(3,5-diamino-4H-1,2,4-triazol-1-ium) 3,4-dioxocyclo-butane-1,2-diolate

Fun HK, Loh WS, Johnson A, Yousuf S, Eno E

Acta Crystallogr Sect E Struct Rep Online, 2013 Mar 1;69(Pt 3):o353-4.

PMID: 23476545 DOI: 10.1107/S160053681300322X

The asymmetric unit of the title compound, 2C2H6N5(+)·C4O4(2-), contains two 3,5-diamino-4H-1,2,4-triazolium cations and one squarate dianion. The squaric acid mol-ecule donated one H atom to each of the two 3,5-diamino-1,2,4-triazole mol-ecules at their N atoms. The squaric acid dianion has four C-O bonds which are shorter than a normal single C-O bond (1.426 Å) and are slightly longer than a normal C=O bond (1.23 Å), which indicates the degree of electron delocalization in the dianion. In the crystal, the cations and dianions are linked by N-H⋯N and N-H⋯O hydrogen bonds into a three-dimensional network.

Fulltext (E)-N'-(3,4-Dihy-droxy-benzyl-idene)-2,4-dimethyl-benzohydrazide monohydrate

Taha M, Ismail NH, Jaafar FM, Aziz AN, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2013 Apr 1;69(Pt 4):o490.

PMID: 23634042 DOI: 10.1107/S1600536813005692

In the title compound, C16H16N2O3·H2O, the dihedral angle between the benzene rings is 30.27 (7)°. In the crystal, the components are linked by N-H⋯O, O-H⋯O and C-H⋯O inter-actions into a three-dimensional network.

Fulltext (E)-2-Meth-oxy-N'-(2,4,6-trihy-droxy-benzyl-idene)benzohydrazide

Taha M, Baharudin MS, Ismail NH, Shah SA, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2013 Feb 1;69(Pt 2):o277.

PMID: 23424550 DOI: 10.1107/S1600536813001748

In the title hydrazone derivative, C(15)H(14)N(2)O(5), the benzene rings are twisted by 7.55 (8)° with respect to each other. The azomethine double bond adopts an E conformation. The mol-ecular structure is stabilized by intra-molecular O-H⋯N and N-H⋯O hydrogen bonds, generating S6 ring motifs. In the crystal, mol-ecules are linked into a three-dimensional network by O-H⋯O hydrogen bonds.

Fulltext (E)-N'-(4-Chloro-benzyl-idene)-2-meth-oxy-benzohydrazide

Baharudin MS, Taha M, Ismail NH, Shah SA, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2013 Feb 1;69(Pt 2):o276.

PMID: 23424549 DOI: 10.1107/S160053681300175X

In the title hydrazone derivative, C(15)H(13)ClN(2)O(2), the dihedral angle between the benzene rings is 2.36 (2)°. An intra-molecular N-H⋯O hydrogen bond is present. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains running parallel to the b axis.

Fulltext (E)-2,4-Dimethyl-N'-(2-methyl-benzyl-idene)benzohydrazide

Taha M, Ismail NH, Jaafar FM, Khan KM, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2013 Mar 1;69(Pt 3):o400.

PMID: 23476582 DOI: 10.1107/S1600536813004388

In the title benzoyl-hydrazide derivative, C17H18N2O, the dihedral angle between the benzene rings is 88.45 (8)° and the azomethine double bond adopts an E conformation. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming a chain along the b axis.

Fulltext N'-[(E)-2,3-Dihy-droxy-benzyl-idene]-2-meth-oxy-benzohydrazide

Taha M, Baharudin MS, Ismail NH, Shah SA, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2012 Dec 1;68(Pt 12):o3256.

PMID: 23468775 DOI: 10.1107/S1600536812042390

The title compound, C15H14N2O4 adopts an E conformation about the azomethine double bond. Intra-molecular N-H⋯O and O-H⋯N hydrogen bonds generate S(6) rings and help to establish the molecular conformation. The dihedral angle between the benzene rings is 17.84 (10)°. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds into a two-dimensional network with a herring-bone pattern arranged parallel to the bc plane.

Fulltext N'-[(E)-2-Hy-droxy-5-meth-oxy-benzyl-idene]-2-meth-oxy-benzohydrazide

Baharudin MS, Taha M, Ismail NH, Shah SA, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2012 Dec 1;68(Pt 12):o3255.

PMID: 23468774 DOI: 10.1107/S1600536812042389

The mol-ecule of the title compound, C16H16N2O4, adopts an E conformation about the azomethine C=N double bond. The dihedral angle formed by the benzene rings is 18.88 (9)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, the mol-ecules are linked into chains parallel to [001] by N-H⋯O hydrogen bonds. The chains are further connected into a three-dimensional network by π-π stacking inter-actions with centroid-centroid distances of 3.6538 (10) and 3.8995 (11) Å.

Fulltext Synthesis of 4-methoxybenzoylhydrazones and evaluation of their antiglycation activity

Taha M, Naz H, Rasheed S, Ismail NH, Rahman AA, Yousuf S, et al.

Molecules, 2014 Jan 21;19(1):1286-301.

PMID: 24451249 DOI: 10.3390/molecules19011286

A series of 4-methoxybenzoylhydrazones 1-30 was synthesized and the structures of the synthetic derivatives elucidated by spectroscopic methods. The compounds showed a varying degree of antiglycation activity, with IC50 values ranging between 216.52 and 748.71 µM, when compared to a rutin standard (IC50=294.46±1.50 µM). Compounds 1 (IC50=216.52±4.2 µM), 3 (IC50=289.58±2.64 µM), 6 (IC50=227.75±0.53 µM), 7 (IC50=242.53±6.1) and 11 (IC50=287.79±1.59) all showed more activity that the standard, and these compounds have the potential to serve as possible leads for drugs to inhibit protein glycation in diabetic patients. A preliminary SAR study was performed.

Fulltext Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones

Taha M, Ismail NH, Jamil W, Yousuf S, Jaafar FM, Ali MI, et al.

Molecules, 2013 Sep 05;18(9):10912-29.

PMID: 24013406 DOI: 10.3390/molecules180910912

2,4-Dimethylbenzoylhydrazones 1-30 were synthesized by condensation reactions of 2,4-dimethylbenzoylhydrazide with various aromatic aldehydes and characterized. The assigned structures of compounds 10, 15 and 22 were further supported by single-crystal X-ray diffraction data. The synthesized compounds were evaluated for their in vitro DPPH radical scavenging activity. They exerted varying degree of scavenging activity toward DPPH radical with IC₅₀ values between 25.6-190 µM. Compounds 1, 4, 2, 3, 7, and 6 have IC₅₀ values of 25.6, 28.1, 29.3, 29.8, 30.0 and 30.1 µM respectively, showing better activity than an n-propyl gallate standard (IC₅₀ value = 30.30 µM). For super oxide anion scavenging activity compounds 1, 2 and 3 with IC₅₀ values of 98.3, 102.6, and 105.6, respectively, also showed better activity than the n-propyl gallate standard (IC₅₀ value = 106.34 µM).

Fulltext 3-[2-(Triphenyl-phosphanyl-idene)acet-yl]-2H-chromen-2-one

Taha M, Ismail NH, Aziza AN, Shah SA, Yousuf S

Acta Crystallogr Sect E Struct Rep Online, 2013 Feb 01;69(Pt 2):o245.

PMID: 23424524 DOI: 10.1107/S160053681300127X

In the title compound, C(29)H(21)O(3)P, a coumarin-substitued ylid, the P atom is linked to three benzene rings and a planar coumarin moiety via a methyl-enecarbonyl group. The bond lengths in the P=C-C=O fragment clearly indicate a delocalized system involving the olefinic and carbonyl bonds. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O inter-action that results in an S7 graph-set ring motif. In the crystal, mol-ecules are linked into a three-dimensional framework by C-H⋯O hydrogen bonds.

Synthesis, in vitro biological activities and in silico study of dihydropyrimidines derivatives

Barakat A, Islam MS, Al-Majid AM, Ghabbour HA, Fun HK, Javed K, et al.

Bioorg Med Chem, 2015 Oct 15;23(20):6740-8.

PMID: 26381063 DOI: 10.1016/j.bmc.2015.09.001

We describe here the synthesis of dihydropyrimidines derivatives 3a-p, and evaluation of their α-glucosidase enzyme inhibition activities. Compounds 3b (IC50=62.4±1.5 μM), 3c (IC50=25.3±1.26 μM), 3d (IC50=12.4±0.15 μM), 3e (IC50=22.9±0.25 μM), 3g (IC50=23.8±0.17 μM), 3h (IC50=163.3±5.1 μM), 3i (IC50=30.6±0.6 μM), 3m (IC50=26.4±0.34 μM), and 3o (IC50=136.1±6.63 μM) were found to be potent α-glucosidase inhibitors in comparison to the standard drug acarbose (IC50=840±1.73 μM). The compounds were also evaluated for their in vitro cytotoxic activity against PC-3, HeLa, and MCF-3 cancer cell lines, and 3T3 mouse fibroblast cell line. All compounds were found to be non cytotoxic, except compounds 3f and 3m (IC50=17.79±0.66-20.44±0.30 μM), which showed a weak cytotoxic activity against the HeLa, and 3T3 cell lines. In molecular docking simulation study, all the compounds were docked into the active site of the predicted homology model of α-glucosidase enzyme. From the docking result, it was observed that most of the synthesized compounds showed interaction through carbonyl oxygen atom and polar phenyl ring with active site residues of the enzyme.

2'-Aryl and 4'-arylidene substituted pyrazolones: As potential α-amylase inhibitors

Yousuf S, Khan KM, Salar U, Chigurupati S, Muhammad MT, Wadood A, et al.

Eur J Med Chem, 2018 Nov 05;159:47-58.

PMID: 30268823 DOI: 10.1016/j.ejmech.2018.09.052

Acarbose and voglibose are well-known α-amylase inhibitors used for the management of type-II diabetes mellitus. Unfortunately, these well-known and clinically used inhibitors are also associated with several adverse effects. Therefore, there is still need to develop the safer therapy. Despite of a broad spectrum of biological significances of pyrazolone, it is infrequently evaluated for α-amylase inhibition. Current study deals with the synthesis and biological screening of aryl and arylidene substituted pyrazolones 1-18 for their potential α-amylase inhibitory activity. Structures of synthetic derivatives 1-18 were identified by different spectroscopic techniques. All compounds 1-18 (IC50 = 1.61 ± 0.16 μM to 2.38 ± 0.09 μM) exhibited significant to moderate inhibitory potential when compared to standard acarbose (IC50 = 1.46 ± 0.26 μM). A number of derivatives including 8-12 (IC50 = 1.68 ± 0.1 μM to 1.97 ± 0.07 μM) and 14-16 (IC50 = 1.61 ± 0.16 μM to 1.93 ± 0.07 μM) were found to be significantly active. Limited SAR suggested that different substitutions on compounds do not have any significant effect on the inhibitory potential. Compounds were found to be mixed-type inhibitors revealed by kinetic studies. However, in silico study was identified a number of key features participating in the interaction with the binding site of α-amylase enzyme.

Fulltext Synthesis, crystal structure, DFT studies and evaluation of the antioxidant activity of 3,4-dimethoxybenzenamine schiff bases

Aziz AN, Taha M, Ismail NH, Anouar el H, Yousuf S, Jamil W, et al.

Molecules, 2014 Jun 19;19(6):8414-33.

PMID: 24950444 DOI: 10.3390/molecules19068414

Schiff bases of 3,4-dimethoxybenzenamine 1-25 were synthesized and evaluated for their antioxidant activity. All the synthesized compounds were characterized by various spectroscopic techniques. In addition, the characterizations of compounds 13, 15 and 16 were supported by crystal X-ray determinations and their geometrical parameters were compared with theoretical DFT calculations at the B3LYP level of theory. Furthermore, the X-ray crystal data of two non-crystalline compounds 8 and 18 were theoretically calculated and compared with the practical values of compounds 13, 15, 16 and found a good agreement. The compounds showed good DPPH scavenging activity ranging from 10.12 to 84.34 μM where compounds 1-4 and 6 showed stronger activity than the standard n-propyl gallate. For the superoxide anion radical assay, compounds 1-3 showed better activity than the standard.

Fulltext Ramadan fasting in people with diabetes and chronic kidney disease (CKD) during the COVID-19 pandemic: The DaR global survey

Hassanein M, Yousuf S, Ahmedani MY, Albashier A, Shaltout I, Yong A, et al.

Diabetes Metab Syndr, 2023 Jul;17(7):102799.

PMID: 37301008 DOI: 10.1016/j.dsx.2023.102799

BACKGROUND AND AIMS: The DaR Global survey was conducted to observe the impact of the COVID-19 pandemic on the intentions to fast and the outcomes of fasting in people with diabetes and chronic kidney disease (CKD).

METHODS: Muslim people with diabetes and CKD were surveyed in 13 countries shortly after the end of Ramadan 2020, using a simple Survey Monkey questionnaire.

RESULTS: This survey recruited 6736 people with diabetes, of which 707 (10.49%) had CKD. There were 118 (16.69%) people with type1 diabetes (T1D), and 589 (83.31%) were with type2 diabetes (T2D). 62 (65.24%) people with T1D and 448 (76.06%) people with T2D had fasted with CKD. Episodes of hypoglycaemia and hyperglycaemia were more frequent among people with T1D compared to T2D, 64.52% and 43.54% vs 25.22% and 22.32% respectively. Visits to the emergency department and hospitalization were more frequent among people with CKD, however no significant difference was found between people with T1D and T2D.

CONCLUSION: The COVID-19 pandemic had only a minor effect on the intention to fast during Ramadan in people with diabetes and CKD. However, hypoglycaemia and hyperglycaemia were found to be more frequent, as well as emergency visits and hospital admissions among people with diabetic kidney disease. Prospective studies are needed in future to evaluate the risk indicators of hypoglycaemia and hyperglycaemia among fasting people with CKD, especially in the context of different stages of kidney disease.

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