Synthesis and pharmacological evaluation of some 3-(4-methoxyphenyl)-2-substitutedamino-quinazolin-4(3H)-ones as analgesic and anti-inflammatory agents

A variety of novel 3-(4-methoxyphenyl)-2-substitutedamino-quinazolin-4(3H)-ones were synthesized by reacting the amino group of 2-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one with a variety of alkyl and aryl ketones. The starting material 2-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one was synthesized from 4-methoxyaniline. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. While the test compounds exhibited significant activity, compounds 2-(1-methylpropylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A1), 2-(1-ethylpropylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A2) and 2-(1-methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent analgesic activity and the compound 2-(1-methylbutylidene)-hydrazino-3-(4-methoxyphenyl)-quinazolin-4(3H)-one (A3) showed moderately more potent anti-inflammatory activity when compared to the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to aspirin.     

The Synthesis of 3-(2'-Hydroxybutyl) isobenzofuran-1 (3H)-one

l（3H】．Isobenzoturans（Dhthalldes】werereDortedtoexhibitawiderangeofbiologicalactivities．Forexample,3－n－butylphthallde（NB）exhibitsantlasthmatlc’,antlconvuls－ant“actlvltles．PenEandZhouhavestudiedonthemetabolismofNBPInrats‘．Theyfoundthat...     

Synthesis and E/Z configuration determination of novel derivatives of 3-aryl-2-(benzothiazol-2'-ylthio) acrylonitrile, 3-(benzothiazol-2'-ylthio)-4-(furan-2'-yl)-3-buten-2-one and 2-(1-(furan-2'-yl)-3'-oxobut-1'-en-2-ylthio)-3-phenylquinazolin-4(3H)-one

Knoevenagel condensation of 2-(benzothiazol-2-ylthio) acetonitrile (2) with either furan-2-carbaldehyde or thiophene-2-carbaldehydes leads to E-isomers 4a-b exclusively, while the condensation of the compound 2 with benzaldehyde or para-substituted benzaldehydes with an electron-donating group afforded E/Z mixtures 4c-e with preferentially formation of the E-isomer. Condensation of furan-2-carbaldehyde (3a) with either 1-(benzothiazol-2'-ylthio) propan-2-one (5) or 2-(2'-oxo propylthio)-3-phenyl-quinazolin-4(3H)-one (9) leads exclusively to the Z-isomers of 6 and 10, respectively. The structures of the newly synthesized compounds were elucidated by elemental analyses, 1H-NMR and 13C-NMR spectra, COSY, HSQC, HMBC, NOE, MS and X-ray crystallographic investigations.     

(5R,6R)-6-苯基-5-(苯磺酰基乙酰基)二环[2.2.1]-2-庚烯的合成及结构表征

报道了一种制备4-苯基-1-苯磺酰基-3-丁烯-2-酮的新合成方法. 4-苯基-3-丁烯-2-酮与溴化试剂Ph₃P^＋CH₂CH₂- COOHBr 作用, 得到1-溴-4-苯基-3-丁烯-2-酮, 不经分离直接与苯亚磺酸钠发生亲核取代反应, 得到4-苯基-1-苯磺酰基-3-丁烯-2-酮. 将此反应产物作为亲双烯体与环戊二烯在手性钛金属催化剂催化下进行不对称Diels-Alder反应, 得到了＞99% ee 的环加成产物(5R,6R)-6-苯基-5-(苯磺酰基乙酰基)二环[2.2.1]-2-庚烯. 用X衍射法对产物的晶体结构进行了测定, 讨论了反应机理, 通过元素分析, NMR, MS对产物的结构进行了表征.     

Preparation and Structure of (E)-1-(3′-Hydroxy-2-Furanyl)-3-(3″-Hydroxy-4″-Methoxyphenyl)-2-Propen-1-One

Abstract

A facile procedure is presented for the synthesis of (E)-1-(3′-hydroxy-2′-furanyl)-3-(3″-hydroxy-4″-methoxyphenyl)-2- propen-1-one (6). Galactosylisomaltol (1) was condensed with isovanillin (2) under strong alkaline conditions at 25 [ddot]C to form (E)-1-(3′-O-β-D-galactopyranosyloxy-2′-furanyl)-3-(3″- hydroxy-4″-methoxyphenyl)-2-propen-1-one (4). (E)-1-(3′-hydroxy-2′-furanyl)-3-(3″-hydroxy-4″-methoxyphenyl)-2-propen-1-one (6) was obtained by acid hydrolysis of 4 in a 53.9% yield. This hetero-cyclic 2-propen-1-one was characterized on the basis of spectral data (IR and ¹H NMR), physicochemical properties, and conversion to a mono-O-acetyl derivative.     

Condensed isoquinolines. 37.* Heterocyclization using 3-(arylamino)- and 3-(hetarylamino)isoquinolin-1(2H)-ones

The reaction of 3-NHR-isoquinolin-1(2H)-ones (R = Ar) with aromatic aldehydes in the presence of Me3SiCl or in acetic acid leads to the formation of derivatives of dibenzo[b,f][1, 8]naphthyridin-5(6H)- one and benzo[f]isoquino[3,4-b][1, 8]naphthyridine-5,9(6H,7H)-dione. The reaction for R = Het in the presence of Me3SiCl gives derivatives of 5H-pyrido[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one, benzo[f]isoquinoline[3,4-b][1,8]naphthyridine-5,9[6H,7H]-dione, and derivatives of new heterocyclic systems, 5H-pyrazino[1',2':1,2]pyrimido[4,5-c]isoquinolin-5-one, 5H-[1,3]thiazolo[3',2':1,2]pyrimido- [4,5-c]isoquinolin-5-one, 5-H-benzo[f]pyrazolo[3,4-b][1,8]naphthyridin-5-one, and isoquino[3,4-b]- [1,5]naphthyridin-5(6H)-one. The effect of the structure of substituent R and nature of the substituent in the benzaldehydes on the structure of the reaction products was studied.     

Synthesis,crystal structure,DFT, molecular docking and antitumor activity of 4-(2-chlorobenzyl)-1-(5-fluoro-2-hydroxy-3-((4-methylpiperidin-1-yl)methyl)phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one

Research on Chemical Intermediates - In this study, the compound 4-(2-chlorobenzyl)-1-(5-fluoro-2-hydroxy-3-((4-methylpiperidin -1-yl)methyl)phenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one (1)...     

Enantiomeric separation of novel anticancer agent 5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one

The enantiomers of 5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one, a novel anticancer agent, were separated by derivatisation with caronaldehyde, separation of the resulting diastereoisomers of the corresponding esters by silica gel column chromatography and regeneration of alcohols (S)-5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one and (R)-5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one under aqueous conditions. The absolute configuration of the enantiomers was determined by 1H NMR studies of the corresponding Mosher esters. Alternatively, the enantiomers were separated by preparative HPLC to collect the (S)- and (R)-5-hydroxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-ones with high purity which was comparable with that obtained by the chemical method. The details of these methods have been presented herein.     

Synthesis,Bioactivity and Crystal Structure Analysis of 2-(Benzo[d]isothiazol-3-yloxy)-N-(3-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl) Acetamide

A novel benzisothiazolin-3-one derivative, 2-(benzo[d]isothiazol-3-yloxy)-N-(3-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl) acetamide(8), was synthesized from the initial compound benzo[d]isothiazol-3(2H)-one(BIT) 1 and 4-fluoroaniline 3. The structure of the target compound 8 was determined by elemental analyses, IR and 1H NMR. The single crystals of intermediate compound 6 and the target compound 8 were obtained and determined by X-ray diffraction analysis. The preliminary biological activity was also evaluated and the results showed the target compound exhibited a good anti-microbial activity.     

Synthesis and spectral studies of cobalt(II), nickel(II) and copper(II) complexes of 1-(2-hydroxy-1-naphthyl)-3-(4-X-phenyl)-2-propen-1-ones and their pyridine adducts

Transition Metal Chemistry - Metal(II) chelates of the type ML2nB [M = CoII, NiII and CuII; L = 1-(2-hydroxy-1-naphthyl)-3-(4-X-phenyl)-2-pro-pen-1-one, (X = H, Cl or Me); B = H2O or Py; n = 0, 2]...     

Reaction of 2-(2-oxoethylidene)furan-3(2H)-ones with isopropylidenehydrazides of aromatic carboxylic acids: Synthesis of 3-hydroxy-3-(2-oxoethyl)-2,3-dihydropyridazin-4(1H)-ones

3-Hydroxy-3-(2-oxoethyl)-6-phenyl-2,3-dihydropyridazin-4(1H)-ones were obtained by the reaction of methyl 3-oxo-5-phenylfuran-2(3H)-ylideneacetate or 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one with benzoic or p-nitrobenzoic isopropylidenehydrazides. Equilibrium C₍₅₎H and C₍₅₎H₂ tautomeric forms were detected in solutions of the 4-chlorophenyl derivatives in DMSO-d₆. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1156–1158, August, 2007.     

2-(2-pyridyl)-3-thioindan-1-one: Synthesis,tautomerism, and complexing properties

Chelate and molecular complexes of 2-(2-pyridyl)-3-thioindan-1-one were prepared. The structure of the ligand (prevalent tautomeric form), including the coordination mode, was proved by ¹H NMR, IR, and EXAFS spectroscopy and by quantum-chemical calculations. The soft-hard properties of the ligand were demonstrated.     

The Reactions of 6-(tert-Butyl)-3-hydrazino-1,2,4-triazin-5(2H)-one with Carbonyl Compounds

The reaction of 6-(tert-butyl)-3-hydrazino-1,2,4-triazin-5(2H)-one with acetone and benzaldehyde yields the corresponding hydrazones. In the presence of thionyl chloride the benzaldehyde hydrazone is converted to 3-(tert-butyl)-6-phenyl-1,2,4-triazolo[4,3-b]-1,2,4-triazin-2(1H)-one and this can also be formed via the acylation of the starting hydrazinotriazinone using benzoyl chloride.     

Crystal Structure of 2-[(P,P-Diphenoxy)phosphono(p-methyl)benzyl]-1, 2-benzisoselenazol-3(2H)-one

The crystal structure of the title compound 2-[(P, P-Diphenoxy)phosphono(p-methyl)benzyl]-1, 2-benzisoselenazol-3(2H)-one, C27H22NO4PSe, was determined by single crystal X-ray diffraction. It crystallizes in the triclinic system, space group P(No. 2) with Mr=534.41, a=9.761(2), b=10.304(2), c=13.396(3), α=110.97(3), β=107.70(3). γ=90.02(3)°, V=1190(1) 3, Z=2, Dx=1.492 g/cm3, λ=0.71073, μ=1.6596 mm-1 and F(000)=544. The structure was solved by direct methods. The final R factor is 0.068 and Rw is 0.074 for 2500 unique observed reflections [I≥3σ(I)]. The results presented herein indicate that the selenium-containing bicyclic moiety is a coplanar structure and that two adjacent molecules are symmetrically linked to each other forming a dimer through the Se(1c)...O=P(1) bonding interaction with an intermolecular Se(1c)...O distance of 2.797 .     

Synthesis of 1-Amino-6,7-dihydro-7-(hydroxymethyl)-4-nitro-pyrrolo[1,2-f]pyrimidin-3-(5H)-one from 2-Amino-6-methylpyrimidin-3-one

The synthesis of previously unreported 1-amino-6,7-dihydro-7-(hydroxymethyl)-4-nitropyrrolo[1,2-f]pyrimidin-3-(5H)-one starting from 2-amino-6-methylpyrimidin-3-one is described.     

3-芳基-1-(吡啶-3-基)-2-(1H-1,2,4-三唑-1-基)-2-丙烯-1-醇的合成及生物活性研究

用硼氢化钠还原3-芳基-1-(吡啶-3-基)-2-(1H-1,2,4-三唑-1-基)丙烯酮, 合成了10个新型含吡啶基的三唑醇类化合物. 所有化合物均经核磁、元素分析确证. 生物活性测试结果表明, 部分化合物具有一定的杀菌活性及植物生长调节活性.     

Formation and structure elucidation of two novel spiro[2H-indol]-3(1H)-ones

The molecular structures of two byproducts 1,1'-diphenyl-3',4'-dihydrodispiro[indole-2,2'-furan-5',2'-indole]-3,3'(1H, 1'H)-dione (3) and 1,5'-diphenyl-4',5'-dihydro-3'H-spiro[indole-2,2'-pyrano[3,2-b]indol]-3(1H)-one (4), which accompanied the rearrangement of 3-hydroxy-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione (1) to 2-hydroxy-2-methyl-1-phenyl-1,2-dihydro-3H-indol-3-one (2), have been elucidated by NMR, MS, and X-ray diffraction.     

[2, 3'-联-1H-吲哚]-3(2H)-酮类化合物的单重态氧反应

[2, 3'-联-1H-吲哚]-3(2H)-酮衍生物(1a~1c)在甲醇中的单重态氧反应给出溶剂捕捉产物4, 后者在分离过程中脱去甲醇分子生成5。考察了标题化合物分子中二氢吲哚酮结构单元以及吲哚结构单元在单重态氧反应中的作用, 并探讨了反应机理。     

Synthesis and Crystal Structure of 3-（2-Hydroxy-phenyl）-5-（2-methylphenyl）-6-thoxycarbonyl-cyclohexen-2-one

1 INTRODUCTION The molecular assembly of one- or multi-dimen-sional aggregation by hydrogen bonds is now an im-portant subject of supramolecular chemistry and crys-tal engineering[1, . Supramolecular structures formed 2]via intermolecular hydrogen bonds X–H…X or C–H…X (X = O, Cl, N, et al.) are very common inorganic compounds[3~12], and they generally possessdifferent properties due to these hydrogen bonds. Concerning about the spectra of benzene-contai-ning…     

SYNTHESIS,CRYSTAL STRUCTURE,AND DFT STUDY OF 1-(PYRROLIDIN-1- YL-METHYL)-4-(THIOPHEN-2-YL-METHYL)- [1,2,4]TRIAZOLO[4,3-a]QUINAZOLIN-5(4H)-ONE

Journal of Structural Chemistry - In this paper, the triazoloquinazolinone derivative 1-(pyrrolidin-1-yl-methyl)-4-(thiophen-2-yl-methyl)[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one is synthesized...