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Fulltext (2-{[1,1-Bis(hy-droxy-meth-yl)-2-oxidoeth-yl]imino-meth-yl}-4-chloro-phenolato-κO,N,O')dibutyl-tin(IV)

Lee SM, Mohd Ali H, Lo KM

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 7):m793.

PMID: 21587717 DOI: 10.1107/S1600536810021872

In the title compound, [Sn(C(4)H(9))(2)(C(11)H(12)BrNO(4))], the Schiff base ligand chelates to the Sn(IV) atom through the two deprotonated hy-droxy groups, as well as through the N atom, to confer an overall cis-C(2)SnNO(2) trigonal-bipyramidal geometry at the Sn(IV) atom [C-Sn-C = 129.92 (9)°]. The remaining methyl-enehy-droxy groups engage in O-H⋯O hydrogen bonding with the O atoms of adjacent mol-ecules, leading to infinite supra-molecular chains propagating in [001].

Fulltext (3Z,3'E)-3,3'-[Cyclo-hexane-1,2-diylbis(aza-nylyl-idene)]bis-(indolin-2-one) N,N-dimethyl-formamide monosolvate dihydrate

Pezeshkpour S, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2012 Jul 1;68(Pt 7):o2107.

PMID: 22798784 DOI: 10.1107/S1600536812026335

In the Schiff base mol-ecule of the title compound, C(22)H(20)N(4)O(2)·C(3)H(7)NO·2H(2)O, the cyclo-hexane ring adopts a chair conformation with the two imine groups linked at the equatorial positions. The two indolin-2-one ring systems make a dihedral angle of 65.63 (5)°. In the crystal, the Schiff base mol-ecules are connected through bifurcated N-H⋯(O,N) hydrogen bonds, forming inversion dimers. The water molecules link the dimers and the dimethylformamide molecules via O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds. Together with C-H⋯π and π-π [centroid-centroid distance = 3.3889 (10) Å] inter-actions a three-dimensional supra-molecular structure is formed.

Fulltext (6E,10E) Isopolycerasoidol and (6E,10E) Isopolycerasoidol Methyl Ester, Prenylated Benzopyran Derivatives from Pseuduvaria monticola Induce Mitochondrial-Mediated Apoptosis in Human Breast Adenocarcinoma Cells

Taha H, Looi CY, Arya A, Wong WF, Yap LF, Hasanpourghadi M, et al.

PLoS One, 2015;10(5):e0126126.

PMID: 25946039 DOI: 10.1371/journal.pone.0126126

Phytochemicals from Pseuduvaria species have been reported to display a wide range of biological activities. In the present study, a known benzopyran derivative, (6E,10E) isopolycerasoidol (1), and a new benzopyran derivative, (6E,10E) isopolycerasoidol methyl ester (2), were isolated from a methanol extract of Pseuduvaria monticola leaves. The structures of the isolated compounds were elucidated by spectroscopic methods including 1D and 2D NMR, IR, UV, and LCMS-QTOF, and by comparison with previously published data. The anti-proliferative and cytotoxic effects of these compounds on human breast cancer cell-lines (MCF-7 and MDA-MB-231) and a human normal breast epithelial cell line (MCF-10A) were investigated. MTT results revealed both (1) and (2) were efficient in reducing cell viability of breast cancer cells. Flow cytometry analysis demonstrated that (1) and (2) induced cell death via apoptosis, as demonstrated by an increase in phosphotidylserine exposure. Both compounds elevated ROS production, leading to reduced mitochondrial membrane potential and increased plasma membrane permeability in breast cancer cells. These effects occurred concomitantly with a dose-dependent activation of caspase 3/7 and 9, a down-regulation of the anti-apoptotic gene BCL2 and the accumulation of p38 MAPK in the nucleus. Taken together, our data demonstrate that (1) and (2) induce intrinsic mitochondrial-mediated apoptosis in human breast cancer cells, which provides the first pharmacological evidence for their future development as anticancer agents.

Fulltext (E)-4-Hydr-oxy-N'-(2-hydr-oxy-4-methoxy-benzyl-idene)benzohydrazide N,N-dimethyl-formamide solvate

Mohd Lair N, Mohd Ali H, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2008 Dec 20;65(Pt 1):o190.

PMID: 21581645 DOI: 10.1107/S160053680804289X

The Schiff base mol-ecule of the title compound, C(15)H(14)N(2)O(4)·C(3)H(7)NO, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is nearly planar (r.m.s. deviation 0.20 Å). The amido N atom is a hydrogen-bond donor to the dimethyl-formamide solvate mol-ecule. One of the hydr-oxy groups forms an intra-molecular hydrogen bond to the N atom of the C=N double bond, whereas the other forms an inter-molecular hydrogen bond to the carbonyl group.

Fulltext (E)-4-Hydr-oxy-N'-(2-hydr-oxy-4-methoxy-benzyl-idene)benzohydrazide monohydrate

Mohd Lair N, Mohd Ali H, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2008;65(Pt 1):o189.

PMID: 21581643 DOI: 10.1107/S1600536808042888

The Schiff base mol-ecule of the title compound, C(15)H(14)N(2)O(4)·H(2)O, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is almost planar (r.m.s. deviation for all non-H atoms = 0.040 Å). The amido N atom is the hydrogen-bond donor to the water mol-ecule, which is the hydrogen-bond donor to the hydr-oxy groups of two neighboring mol-ecules. One of the hydroxyl groups acts as an intra-molecular and the other as an inter-molecular hydrogen-bond donor.

Fulltext (E)-N'-(2,4-Dihy-droxy-benzyl-idene)-4-nitro-benzohydrazide

Mohd Lair N, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2011;67(Pt 2):o459.

PMID: 21523120 DOI: 10.1107/S1600536811002224

The title compound, C(14)H(11)N(3)O(5), is essentially planar, with an r.m.s. deviation for the non-H atoms of 0.0832 (3) Å. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link adjacent mol-ecules into layers parallel to (101). These layers are further connected into a three-dimensional network via C-H⋯O inter-actions. In addition, a π-π inter-action occurs between the aromatic rings [centroid-centroid distance = 3.5425 (8) Å]. An intra-molecular O-H⋯N hydrogen bond is also observed.

Fulltext (E)-N'-(5-Bromo-2-hy-droxy-benzyl-idene)-3,5-dihy-droxy-benzohydrazide monohydrate

Saharin SM, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 8):o2045.

PMID: 21588352 DOI: 10.1107/S1600536810027856

The Schiff base mol-ecule in the title compound, C(14)H(11)BrN(2)O(4)·H(2)O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.16 Å. In the crystal structure, the Schiff base mol-ecules and the water mol-ecules are linked together by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, leading to layers parallel to the bc plane. An intra-molecular O-H⋯N hydrogen bond involving the imine N atom and a hy-droxy substituent is also observed.

Fulltext 1,5-Bis(2-oxoindolin-3-yl-idene)thio-carbonohydrazide tetra-hydro-furan monosolvate

Pezeshkpour S, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2012 Jun 1;68(Pt 6):o1870.

PMID: 22719632 DOI: 10.1107/S1600536812022714

In the thio-carbonohydrazide mol-ecule of the title compound, C(17)H(12)N(6)O(2)S·C(4)H(8)O, the terminal indolin-2-one ring systems make a dihedral angle of 20.13 (6)° with each other. Two intra-molecular N-H⋯O hydrogen bonds are present, each of which generates an S(6) ring. In the crystal, N-H⋯O hydrogen bonds lead to a mol-ecular chain running along the b axis. The tetra-hydro-furan solvent mol-ecule is disordered over two orientations in a 0.561 (11):0.439 (11) ratio.

Fulltext 2,6-Diamino-4-oxo-3,4-dihydropyrim-idin-1-ium chloride dihydrate

Suleiman Gwaram N, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2010 Aug 11;66(Pt 9):o2294.

PMID: 21588646 DOI: 10.1107/S1600536810031557

In the crystal structure of the title compound, C(4)H(7)N(4)O(+)·Cl(-)·2H(2)O, adjacent cations are connected to one another through N-H⋯O hydrogen bonds, forming infinite chains along the b axis. These chains are further hydrogen bonded to the chloride anions and water mol-ecules, resulting in a three-dimensional network. The pyrimidine rings of adjacent mol-ecules are arranged in an anti-parallel manner above each other with centroid-centroid distances of 3.435 (1) Å, indicative of π-π inter-actions.

Fulltext 2-Methyl-benzimidazolium thio-cyanate

A Shaker S, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 11):o2913.

PMID: 21589087 DOI: 10.1107/S1600536810042145

In the crystal structure of the title compound, C(8)H(9)N(2) (+)·SCN(-), the nearly planar 2-methyl-benzimidazolium cation [r.m.s. deviation = 0.0123 (4) Å] is perpendicular to a mirror plane and the methyl H atoms are disordered about the mirror plane with equal occupancies. The thio-cyanate anion also lies on a mirror plane. N-H⋯N hydrogen bonds link the components into an infinite chain along the b axis.

Fulltext 2-Methyl-benzimidazolium thio-cyanate-2-methyl-benzimidazole (1/1)

A Shaker S, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2010;66(Pt 9):o2291.

PMID: 21588643 DOI: 10.1107/S1600536810031181

In the crystal structure of the title compound, C(8)H(9)N(2) (+)·SCN(-)·C(8)H(8)N(2), the three components are linked by inter-molecular N-H⋯N and N-H⋯S hydrogen bonds into infinite chains along the c axis.

Fulltext 3,4,5-Trihy-droxy-benzohydrazidium perchlorate-3,4,5-trihy-droxy-benzohydrazide-water (1/1/1)

A Alhadi A, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2011 Sep 1;67(Pt 9):o2229-30.

PMID: 22058903 DOI: 10.1107/S1600536811030595

The crystal studied of the title compound, C(7)H(9)N(2)O(4) (+)·ClO(4) (-)·C(7)H(8)N(2)O(4)·H(2)O, was found to be a racemic twin with a 0.72 (18):0.28 (18) domain ratio. The hydrazidium group is close to planar, with an r.m.s deviation of 0.105 Å; the hydrazide group deviates more from planarity, with an r.m.s deviation of 0.174 Å. In the crystal, the hydrazidium cation, hydrazide mol-ecule, perchlorate anions and water mol-ecules are linked through O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds into a three-dimensional supra-molecular network. In addition, the benzene rings of the hydrazidium and hydrazide units are connected via π-π inter-actions into infinite chains along the c axis; the centroid-centroid distances are 3.486 (3) and 3.559 (3) Å.

Fulltext 3,4,5-Trihydr-oxy-N'-(1H-indol-3-yl-methyl-idene)benzohydrazide penta-hydrate

Khaledi H, Mohd Ali H, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2008;64(Pt 12):o2481.

PMID: 21581446 DOI: 10.1107/S1600536808039342

The two aromatic parts of the title compound, C(16)H(13)N(3)O(4)·5H(2)O, are connected through a conjugated -CH=N-NH-C(O)- fragment, giving an almost planar mol-ecule. The organic mol-ecules and uncoordinated water mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds into a three-dimensional network.

Fulltext 5-Meth-oxy-2-[(2-morpholinoeth-yl)-iminio-meth-yl]phenolate

Mohd Lair N, Mohd Ali H, Ng SW

Acta Crystallogr Sect E Struct Rep Online, 2009;65(Pt 5):o1067.

PMID: 21583883 DOI: 10.1107/S1600536809013786

Each of the two independent mol-ecules of the title comound, C(14)H(20)N(2)O(3), exists in the zwitterionic form as the imino N atoms are protonated. The =N-H unit forms an intra-molecular hydrogen bond to the negatively charged O atom, and also a weaker intermolecular N-H⋯O bond, the latter resulting in inversion dimers.

Fulltext 5-Methyl-1H-indole-3-carbaldehyde

Ismail SS, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2012 Sep 1;68(Pt 9):o2691.

PMID: 22969583 DOI: 10.1107/S1600536812034873

The title mol-ecule, C(10)H(9)NO, is almost planar with an r.m.s. deviation for all non-H atoms of 0.0115 Å. In the crystal, mol-ecules are connected through N-H⋯O hydrogen bonds into chains running along [021]. The chains are further connected via C-H⋯π inter-actions, forming layers in the bc plane.

Fulltext Acute toxicity and gastroprotection studies of a new schiff base derived copper (II) complex against ethanol-induced acute gastric lesions in rats

Hajrezaie M, Golbabapour S, Hassandarvish P, Gwaram NS, A Hadi AH, Mohd Ali H, et al.

PLoS One, 2012;7(12):e51537.

PMID: 23251568 DOI: 10.1371/journal.pone.0051537

BACKGROUND: Copper is an essential element in various metabolisms. The investigation was carried out to evaluate acute gastroprotective effects of the Copper (II) complex against ethanol-induced superficial hemorrhagic mucosal lesions in rats.

METHODOLOGY/PRINCIPAL FINDINGS: Rats were divided into 7 groups. Groups 1 and 2 were orally administered with Tween 20 (10% v/v). Group 3 was orally administered with 20 mg/kg omeprazole (10% Tween 20). Groups 4-7 received 10, 20, 40, and 80 mg/kg of the complex (10% Tween 20), respectively. Tween 20 (10% v/v) was given orally to group 1 and absolute ethanol was given orally to groups 2-7, respectively. Rats were sacrificed after 1 h. Group 2 exhibited severe superficial hemorrhagic mucosal lesions. Gastric wall mucus was significantly preserved by the pre-treatment complex. The results showed a significant increase in glutathione (GSH), superoxide dismutase (SOD), nitric oxide (NO), and Prostaglandin E2 (PGE(2)) activities and a decrease in malondialdehyde (MDA) level. Histology showed marked reduction of hemorrhagic mucosal lesions in groups 4-7. Immunohistochemical staining showed up-regulation of Hsp70 and down-regulation of Bax proteins. PAS staining of groups 4-7 showed intense stain uptake of gastric mucosa. The acute toxicity revealed the non-toxic nature of the compound.

CONCLUSIONS/SIGNIFICANCE: The gastroprotective effect of the Copper (II) complex may possibly be due to preservation of gastric wall mucus; increase in PGE(2) synthesis; GSH, SOD, and NO up-regulation of Hsp70 protein; decrease in MDA level; and down-regulation of Bax protein.

Fulltext Aqua-chloridobis(2-{[3-(morpholin-4-yl)prop-yl]imino-meth-yl}phenolato)manganese(III) monohydrate

Ikmal Hisham NA, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2011 Aug 1;67(Pt 8):m1044-5.

PMID: 22090835 DOI: 10.1107/S1600536811026493

In the title compound, [Mn(C(14)H(19)N(2)O(2))(2)Cl(H(2)O)]·H(2)O, the Mn(III) atom is N,O-chelated by two monoanionic Schiff bases, forming two six-membered chelate rings. One Cl atom and one water mol-ecule in trans positions complete a distorted octa-hedral geometry around the metal atom. In the crystal, the complex mol-ecules and the uncoordinated water mol-ecules are connected via O-H⋯N, O-H⋯O and O-H⋯Cl hydrogen bonds into layers parallel to the ac plane and these are consolidated by C-H⋯π inter-actions. The layers are further linked into a three-dimensional network through C-H⋯O inter-actions.

Fulltext Aqua-{2-morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}bis-(thio-cyanato-κN)cobalt(II)

Suleiman Gwaram N, Ikmal Hisham NA, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2011 Jan 15;67(Pt 2):m205.

PMID: 21522869 DOI: 10.1107/S160053681100136X

In the title complex, [Co(NCS)(2)(C(13)H(19)N(3)O)(H(2)O)], the Co(II) ion is six-coordinated by the N,N',N''-tridentate Schiff base, the N atoms of two thio-cyanate ligands and one water mol-ecule in a distorted octa-hedral geometry. Intra-molecular C-H⋯N and C-H⋯O hydrogen bonds occur. In the crystal, inter-molecular O-H⋯O, O-H⋯S, C-H⋯S and S⋯S [3.5546 (18) Å] inter-actions result in an infinite three-dimensional network.

Fulltext Aqua-{2-morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}bis-(thio-cyanato-κN)nickel(II)

Suleiman Gwaram N, Ikmal Hisham NA, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2010 Dec 24;67(Pt 1):m108.

PMID: 21522521 DOI: 10.1107/S1600536810052578

In the title compound, [Ni(NCS)(2)(C(13)H(19)N(3)O)(H(2)O)], the Ni(II) ion is six-coordinated by the N,N',N''-tridentate Schiff base, the N atoms of two thio-cyanate ligands and one water O atom in a distorted octa-hedral geometry. Intra-molecular C-H⋯N and C-H⋯O hydrogen bonds occur. In the crystal, O-H⋯S, O-H⋯O and C-H⋯S hydrogen bonds link adjacent mol-ecules into layers parallel to the ac plane.

Fulltext Aqua-{N,N-dimethyl-N'-[1-(2-pyrid-yl)ethyl-idene]ethane-1,2-diamine-κN,N',N''}bis-(thio-cyanato-κN)nickel(II)

Suleiman Gwaram N, Saharin SM, Khaledi H, Mohd Ali H

Acta Crystallogr Sect E Struct Rep Online, 2011 Apr 01;67(Pt 4):m513.

PMID: 21754017 DOI: 10.1107/S1600536811011512

In the title compound, [Ni(NCS)(2)(C(11)H(17)N(3))(H(2)O)], the Ni(II) ion is six-coordinated by the N,N',N"-tridentate Schiff base N atoms, two cis-positioned N-bound isothio-cyanate groups and one water mol-ecule. In the crystal, O-H⋯S hydrogen bonds link adjacent mol-ecules into infinite layers parallel to the ac plane. The layers are further connected into a three-dimensional network via C-H⋯π inter-actions. The -CH(2)-N(CH(3))(2) fragment is disordered over two sets of sites in a 0.556 (5):0.444 (5) ratio.

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