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1.  1-(2-Methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl acetate 
In the title compound, C9H13N3O4, an ester of the anti-infection drug secnidazole, the dihedral angle between the nitro­imidazole mean plane (r.m.s. deviation = 0.028 Å) and the pendant acetate group is 43.17 (11)°. In the crystal, inversion dimers linked by pairs of C—H⋯O inter­actions generate R 2 2(10) loops and further C—H⋯O hydrogen bonds link the dimers into [100] chains. Weak aromatic π–π stacking inter­actions with a centroid–centroid distance of 3.7623 (11) Å are also observed.
doi:10.1107/S1600536814002505
PMCID: PMC3998449  PMID: 24765001
2.  2-{[2-(2-Hy­droxy-5-meth­oxy­benzyl­idene)hydrazin-1-yl­idene]meth­yl}-4-meth­oxy­phenol 
The title phenyl­hydrazine 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). Intra­molecular O—H⋯N hydrogen bonds are observed, generating S(6) graph-set ring motifs.
doi:10.1107/S1600536813034636
PMCID: PMC3998297  PMID: 24764858
3.  2,6-Di­fluoro-N-(prop-2-yn­yl)benzamide 
In the mol­ecule of the title di­fluoro­benzamide derivative, C10H7F2NO, the angle formed by the least-squares mean line through the prop-2-ynyl group [maximum deviation = 0.011 (3) Å] and the normal to the benzene ring is 59.03 (7)°. In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯F hydrogen bonds into layers parallel to the ac plane.
doi:10.1107/S1600536813021120
PMCID: PMC3884469  PMID: 24427068
4.  3,4-Di­methyl­thieno[2,3-b]thio­phene-2,5-dicarbo­nitrile 
The asymmetric unit of the title compound, C10H6N2S2, contains two crystallographically independent but conformationally similar mol­ecules. The fused thio­phene ring cores are almost planar [maximum deviation = 0.027 (3) Å] with the thio­phene rings forming dihedral angles of 0.5 (4)° in one mol­ecule and 1.91 (4)° in the other. The crystal packing is stabilized only by van der Waals inter­actions.
doi:10.1107/S1600536813017960
PMCID: PMC3793767  PMID: 24109354
5.  Synthesis, reactions and biological activity of some new bis-heterocyclic ring compounds containing sulphur atom 
Background
The derivatives of thieno[2,3-b]thiophene belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial application.
Results
A new building block with two electrophilic center of thieno[2,3-b]thiophene derivatives 2 has been reported by one-pot reaction of diketone derivative 1 with Br2/AcOH in excellent yield. A variety of heteroaromatics having bis(1H-imidazo[1,2a] benzimidazole), bis(1H-imidazo[1,2-b][1,2,4]triazole)-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives, dioxazolo-, dithiazolo-, and 1H-imidazolo-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives as well pyrrolo, thiazolo -3-methyl-4-phenylthieno[2,3-b]thiophene derivatives have been designed, synthesized, characterized, and evaluated for their biological activity. Compounds 3–9 showed good bioassay result. These new derivatives were evaluated for anti-cancer activity against PC-3 cell lines, in vitro antioxidant potential and β-glucuronidase and α-glucosidase inhibitory activities. Compound 3 (IC50 = 56.26 ± 3.18 μM) showed a potent DPPH radical scavenging antioxidant activity and found to be more active than standard N-acetylcystein (IC50 = 105.9 ± 1.1 μM). Compounds 8a (IC50 = 13.2 ± 0.34 μM) and 8b (IC50 = 14.1 ± 0.28 μM) found as potent inhibitor of α-glucusidase several fold more active than the standard acarbose (IC50 = 841 ± 1.73 μM). Most promising results were obtained in β-glucuronidase enzyme inhibition assay. Compounds 5 (IC50 = 0.13 ± 0.019 μM), 6 (IC50 = 19.9 ± 0.285 μM), 8a (IC50 = 1.2 ± 0.0785 μM) and 9 (IC50 = 0.003 ± 0.09 μM) showed a potent inhibition of β-glucuronidase. Compound 9 was found to be several hundred fold more active than standard D-Saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM).
Conclusions
Synthesis, characterization, and in vitro biological activity of a series of thieno[2,3-b]thiophene have been investigated.
doi:10.1186/1752-153X-7-112
PMCID: PMC3728144  PMID: 23829861
Thienothiophene; Oxazole; Imidazole; Thiazole; Bisheterocycles; β-glucuronidase inhibition; α-glucosidase inhibition; DPPH radical scavenging activity; Ctotoxicity; Cancer cell line
6.  Ethyl 4-acetyl-5-anilino-3-methyl­thio­phene-2-carboxyl­ate 
In the title compound, C16H17NO3S, a thio­phene derivative with amino phenyl, acetyl, methyl and ethyl carboxyl susbtituents attached to a central thio­phene ring, the phenyl and thio­phene rings form a dihedral angle of 36.92 (9) Å. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, which forms an S(6) ring motif.
doi:10.1107/S160053681301547X
PMCID: PMC3772481  PMID: 24046624
7.  Dimethyl 2-(4-methyl­benzyl­idene)malonate 
In the mol­ecule of the title compound, C13H14O4, the benzene ring forms dihedral angles of 18.60 (7) and 81.36 (8)° with the two arms of the malonate moiety. The crystal structure features C—H⋯O inter­actions, which form chains running parallel to the b axis.
doi:10.1107/S1600536813012464
PMCID: PMC3685070  PMID: 23795089
8.  1-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetone 
In the mol­ecule of the title compound, C7H9N3O3, the nitro and carbonyl groups are tilted with respect to the imidazole ring by 9.16 (6) and 65.47 (7)°, respectively. Neighbouring chains are linked via C—H⋯N and C—H⋯O hydrogen bonds forming two-dimensional slab-like networks lying parallel to (01-1).
doi:10.1107/S1600536813006569
PMCID: PMC3629604  PMID: 23634091
9.  (E)-N′-(3,4-Dihy­droxy­benzyl­idene)-2,4-dimethyl­benzohydrazide monohydrate 
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 inter­actions into a three-dimensional network.
doi:10.1107/S1600536813005692
PMCID: PMC3629524  PMID: 23634042
10.  (E)-2,4-Dimethyl-N′-(2-methyl­benzyl­idene)benzohydrazide 
In the title benzoyl­hydrazide 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, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming a chain along the b axis.
doi:10.1107/S1600536813004388
PMCID: PMC3588470  PMID: 23476582
11.  5-Chloro-2-(4-meth­oxy­phen­yl)-1,3-benzo­thia­zole 
In the title compound, C14H10ClNOS, the dihedral angle between the benzothia­zole ring system and the meth­oxy-substituted benzene ring is 8.76 (16)°. In the crystal, mol­ecules are stacked in columns along the c axis and no significant inter­molecular inter­actions are observed.
doi:10.1107/S1600536813001955
PMCID: PMC3588450  PMID: 23476550
12.  (E)-Ethyl 2-anilino-5-[3-(dimethyl­amino)­acrylo­yl]-4-phenyl­thio­phene-3-carboxyl­ate 
In the title compound, C24H24N2O3S, the phenyl rings form dihedral angles of 55.65 (11) and 79.60 (11)° with the plane of the thio­phene ring. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, centrosymmetrically related mol­ecules are linked into dimers by two pairs of C—H⋯O inter­actions.
doi:10.1107/S1600536813003231
PMCID: PMC3588423  PMID: 23476543
13.  Bis­(3,5-diamino-4H-1,2,4-triazol-1-ium) 3,4-dioxocyclo­butane-1,2-diolate 
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 mol­ecule donated one H atom to each of the two 3,5-diamino-1,2,4-triazole mol­ecules 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.
doi:10.1107/S160053681300322X
PMCID: PMC3588514  PMID: 23476545
14.  (E)-N′-(4-Chloro­benzyl­idene)-2-meth­oxy­benzohydrazide 
In the title hydrazone derivative, C15H13ClN2O2, the dihedral angle between the benzene rings is 2.36 (2)°. An intra­molecular N—H⋯O hydrogen bond is present. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the b axis.
doi:10.1107/S160053681300175X
PMCID: PMC3569803  PMID: 23424549
15.  (E)-2-Meth­oxy-N′-(2,4,6-trihy­droxy­benzyl­idene)benzohydrazide 
In the title hydrazone derivative, C15H14N2O5, the benzene rings are twisted by 7.55 (8)° with respect to each other. The azomethine double bond adopts an E conformation. The mol­ecular structure is stabilized by intra­molecular O—H⋯N and N—H⋯O hydrogen bonds, generating S6 ring motifs. In the crystal, mol­ecules are linked into a three-dimensional network by O—H⋯O hydrogen bonds.
doi:10.1107/S1600536813001748
PMCID: PMC3569804  PMID: 23424550
16.  3-[2-(Triphenyl­phosphanyl­idene)acet­yl]-2H-chromen-2-one 
In the title compound, C29H21O3P, a coumarin-substitued ylid, the P atom is linked to three benzene rings and a planar coumarin moiety via a methyl­enecarbonyl group. The bond lengths in the P=C–C=O fragment clearly indicate a delocalized system involving the olefinic and carbonyl bonds. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O inter­action that results in an S7 graph-set ring motif. In the crystal, mol­ecules are linked into a three-dimensional framework by C—H⋯O hydrogen bonds.
doi:10.1107/S160053681300127X
PMCID: PMC3569778  PMID: 23424524
17.  2-{[(Dimethyl­amino)­methyl­idene]amino}-5-nitro­benzonitrile 
The title mol­ecule, C10H10N4O2, is almost planar and adopts an E configuration of the azomethine [C=N = 1.298 (2) Å] double bond. The benzene ring is attached to an essentially planar (r.m.s. deviation = 0.0226 Å) amidine moiety (N=CN/Me2), the dihedral angle between the two mean planes being 18.42 (11)°. The cyano group lies in the plane of the benzene ring [the C and N atoms deviating by 0.030 (3) and 0.040 (3) Å, respectively], while the nitro group makes a dihedral angle 5.8 (3)° with the benzene ring. There are two distinct inter­molecular hydrogen bonds, C—H⋯O and C—H⋯N, that stabilize the crystal structure; the former inter­actions result in centrosymmetric dimers about inversion centers resulting in ten-membered rings, while the later give rise to chains of mol­ecules running parallel to the b axis.
doi:10.1107/S1600536812048866
PMCID: PMC3588379  PMID: 23476456
18.  Synthesis of some potent immunomodulatory and anti-inflammatory metabolites by fungal transformation of anabolic steroid oxymetholone 
Background
Biotransformation of organic compounds by using microbial whole cells provides an efficient approach to obtain novel analogues which are often difficult to synthesize chemically. In this manuscript, we report for the first time the microbial transformation of a synthetic anabolic steroidal drug, oxymetholone, by fungal cell cultures.
Results
Incubation of oxymetholone (1) with Macrophomina phaseolina, Aspergillus niger, Rhizopus stolonifer, and Fusarium lini produced 17β-hydroxy-2-(hydroxy-methyl)-17α-methyl-5α-androstan-1-en-3-one (2), 2α,17α-di(hydroxyl-methyl)-5α-androstan-3β,17β-diol (3), 17α-methyl-5α-androstan-2α,3β,17β-triol (4), 17β-hydroxy-2-(hydroxymethyl)-17α-methyl-androst-1,4-dien-3-one (5), 17β-hydroxy-2α-(hydroxy-methyl)-17α-methyl-5α-androstan-3-one (6), and 2α-(hydroxymethyl)-17α-methyl-5α-androstan-3β-17β-diol (7). Their structures were deduced by spectral analyses, as well as single-crystal X-ray diffraction studies. Compounds 2–5 were identified as the new metabolites of 1. The immunomodulatory, and anti-inflammatory activities and cytotoxicity of compounds 1–7 were evaluated by observing their effects on T-cell proliferation, reactive oxygen species (ROS) production, and normal cell growth in MTT assays, respectively. These compounds showed immunosuppressant effect in the T-cell proliferation assay with IC50 values between 31.2 to 2.7 μg/mL, while the IC50 values for ROS inhibition, representing anti-inflammatory effect, were in the range of 25.6 to 2.0 μg/mL. All the compounds were found to be non-toxic in a cell-based cytotoxicity assay.
Conclusion
Microbial transformation of oxymetholone (1) provides an efficient method for structural transformation of 1. The transformed products were obtained as a result of de novo stereoselective reduction of the enone system, isomerization of double bond, insertion of double bond and hydroxylation. The transformed products, which showed significant immunosuppressant and anti-inflammatory activities, can be further studied for their potential as novel drugs.
doi:10.1186/1752-153X-6-153
PMCID: PMC3740782  PMID: 23237028
Oxymetholone; Anabolic steroid; Biotransformation; de novo Hydroxylation; Immunomodulation; T-Cell proliferation inhibition; Anti-inflammation; Inhibition of reactive oxygen species production; 3T3 Fibroblast cells
19.  N-(2,5-Dimeth­oxy­phen­yl)-6-nitro­quinazolin-4-amine 
In the title mol­ecule, C16H14N4O4, the quinazoline ring is substanti­ally planar (r.m.s. deviation = 0.0129 Å) and forms a dihedral angle of 2.73 (8)° with the benzene ring. The conformation of the mol­ecule is stabilized by an intra­molecular C—H⋯N hydrogen bond. In the crystal, mol­ecules are linked into chains running parallel to the b axis by C—H⋯O hydrogen bonds. In addition, π–π stacking is observed between dimethoxy-substituted and nitro-substituted benzene rings, with centroid–centroid distances in the range 3.6438 (10)–3.7148 (10) Å.
doi:10.1107/S1600536812048878
PMCID: PMC3588306  PMID: 23476461
20.  N′-(3-Chloro­benzyl­idene)-4-hy­droxy­benzohydrazide 
The mol­ecule of the title compound, C14H11ClN2O2 adopts an E conformation of the azomethine double bond and the dihedral angle between the benzene rings is 38.96 (13)°. In the crystal, mol­ecules are linked by N—H⋯O and O—H⋯O (with the ketone O atom as acceptor) and C—H⋯O (with the hy­droxy O atom as acceptor) hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536812048325
PMCID: PMC3589070  PMID: 23476306
21.  3-(2-Ethyl-2-phenyl­hydrazin-1-yl­idene)indolin-2-one 
In the title compound, C16H15N3O, the dihedral angle between the indole ring system (r.m.s. deviation = 0.020 Å) and the phenyl ring is 14.49 (9)°. The mol­ecular conformation is supported by an intra­molecular C—H⋯O inter­action, which closes an S(7) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops.
doi:10.1107/S1600536812047988
PMCID: PMC3589046  PMID: 23476282
22.  N′-[(E)-2-Hy­droxy-5-meth­oxy­benzyl­idene]-2-meth­oxy­benzohydrazide 
The mol­ecule 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 mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, the mol­ecules 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 inter­actions with centroid–centroid distances of 3.6538 (10) and 3.8995 (11) Å.
doi:10.1107/S1600536812042389
PMCID: PMC3588809  PMID: 23468774
23.  N′-[(E)-2,3-Dihy­droxy­benzyl­idene]-2-meth­oxy­benzohydrazide 
The title compound, C15H14N2O4 adopts an E conformation about the azomethine double bond. Intra­molecular 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, mol­ecules 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.
doi:10.1107/S1600536812042390
PMCID: PMC3588810  PMID: 23468775
24.  4-Meth­oxy-N-(4-meth­oxy-2-nitro­phen­yl)benzamide 
In the title compound, C15H14N2O5, the central amide C—C(=O)—N—C unit forms dihedral angles of 28.17 (13) and 26.47 (13)° with the two benzene rings, whereas the two benzene rings are almost coplanar, making a dihedral angle of 4.52 (13)°. The two meth­oxy and the nitro substituents are almost coplanar with their attached benzene rings, with C—O—C—C torsion angles of −1.3 (4) and −4.6 (4)°, and an O—N—C—C torsion angle of 17.1 (3)°. In the crystal, mol­ecules are linked via C—H⋯O and N—H⋯O inter­actions, forming a tape running along the b axis.
doi:10.1107/S1600536812037701
PMCID: PMC3470382  PMID: 23125795
25.  5-Chloro-2-(3,4,5-trimeth­oxy­phen­yl)-1,3-benzothia­zole 
In the title compound, C16H14ClNO3S, the dihedral angle between the almost-planar benzothia­zole ring system [maximum deviation = 0.012 (3) Å] and the aromatic ring of the trimeth­oxy­phenyl group is 15.56 (6)°. In the crystal, the mol­ecules are arranged into layers parallel to the bc plane, held together only by weak van der Waals forces.
doi:10.1107/S1600536812039372
PMCID: PMC3470404  PMID: 23125817

Results 1-25 (58)