SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME 6-ARYLIDENE-3-ARYL-2,3,3a,4,5,6-HEXAHYDROCYCLOPENTA [c] PYRAZOLES/OXAZOLES

被引：0
|
作者：
Azam, Md. Afzal [1 ]
Gomathy, S. [1 ]
Alam, F. [1 ]
Suresh, B. [1 ]
机构：
[1] JSS Coll Pharm, Dept Pharmaceut Chem, Ootacamund 643001, Tamil Nadu, India
来源：
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 18卷 / 02期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Condensation of alpha,alpha-bis (arylidene) cycloalkanones 1a,b with hydrazine hydrochloride in presence of gl acetic acid gave 6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta[e] pyrazoles 2a,b which on Mannich condensation with various alkyl and aryl amines yielded 2-aminomethyl-6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta[c] pyrazoles 5a-g. Condensation of 1 a,b with hydroxylamine hydrochloride in alcohol resulted in the formation of 6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta[c] oxazoles 4a,b. Further, compounds la,b undergo cyclization with phenylhydrazine hydrochloride/2,4-dinitro phenylhydrazine hydrochloride in presence of sodium acetate and gl acetic acid to furnish 2-(phenyl/2,4-dinitrophenyl)-6-arylidene-3-aryl-2,3,3a,4,5,6-hexahydrocyclopenta [c] pyrazoles 3a-d. The structures of the compounds have been established based on their analytical and spectral data. All the compounds have been evaluated in vitro for their antibacterial and antifungal activities. Compounds 2b, 5c and 5d exhibited significant antibacterial activity.
引用
收藏
页码：157 / 160
页数：4
相关论文
共 50 条
  • [31] Behavior of hydrazonoyl chlorides towards the C=N double bond of Δ2-pyrazolines.: A study on 2-(4-nitrophenyl)-2,3,3a,4,5,6-hexahydro-6-oxofuro[3,4-c]pyrazole
    Molteni, G
    Garanti, L
    HETEROCYCLES, 2001, 55 (08) : 1573 - 1580
  • [32] Synthesis and theoretical study of 2-amino-2,3,3a,4,5,6-hexahydro-1H-phenalene and its biological evaluation on central dopaminergic system
    Angel-Guío, JE
    Charris, JE
    Pérez, J
    de Pérez, ZD
    Compagnone, R
    Israel, A
    Orfila, L
    de Angel, BM
    López, SE
    Rodríguez, L
    Caldera, J
    de Báez, EM
    FARMACO, 2000, 55 (9-10): : 575 - 582
  • [33] Synthesis of 2,3,3a,4,5,6-Hexahydrobenzo[b]thiophene-3a-carbaldehydes via a Tandem Reaction of Cyclic β-Thiocyanatoenals with Electron-Deficient Alkenes Triggered by Fluoride
    Zhang, Min
    Gong, Yuefa
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (02) : 573 - 577
  • [34] Synthesis of 5-arylidene-2-aryl-3-(benzotriazoloacetamidyl)-1,3-thiazolidin-4-ones as analegesic and antimicrobial agents
    Asati, KC
    Srivastava, SK
    Srivastava, SD
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2006, 45 (02): : 526 - 531
  • [35] SYNTHESIS OF 5-ARYL-1, 5-DIHYDRO-6-NITROPYRAZOLO[4,3-C]PYRAZOLES AND THEIR BIOLOGICAL-ACTIVITY
    PATEL, HV
    FERNANDES, PS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1989, 28 (01): : 56 - 60
  • [36] 3A,6A-DIMETHYL-2,3,3A,5,6,6A-HEXAHYDROFURO[3,2-B]FURAN-2,5-DIONE, C8H10O4
    CAIRA, MR
    WATSON, WH
    KAGAN, J
    SINGH, SP
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1984, 40 (MAR) : 498 - 500
  • [37] Synthesis and 1H and 13C NMR study of the stereochemistry of (E)-2-acetyl-3-aryl-7-arylidene-3,3a,4,5,6,7-hexahydroindazoles
    Vijayabaskar, V
    Perumal, S
    Selvaraj, S
    Hewlins, MJE
    MAGNETIC RESONANCE IN CHEMISTRY, 1999, 37 (01) : 65 - 68
  • [38] Synthesis of N-haloarylsulphonyl-3-alkyl/aryl-5-(4-haloaryl), pyrazoles, N-aroyl-3-alkyl/aryl-5-(4-haloaryl)-pyrazoles, bis (N′-pyrazolyl) alkanediones and their antimicrobial activities
    Pathak, Vijai N.
    Joshi, Rahul
    Chabra, Supreet
    Tiwari, Ranjana
    Sharma, Jaimala
    Gupta, Neetu
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 17 (02) : 139 - 144
  • [39] Synthesis, spectral studies and antimicrobial activity of 7-chloro-2-alkyl/aryl-4-alkyl/aryl-3arylidene-3H-1,5-benzodiazepines
    Pathak, Vijai N.
    Joshi, Rahul
    Gupta, Neetu
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2007, 46 (07): : 1191 - 1197
  • [40] FACILE SYNTHESIS OF (3AS)-1,3A-DIMETHYL-2,3,3A,5,6,7-HEXAHYDROINDEN-4(5H)-ONE, AN INTERMEDIATE FOR STEROID-SYNTHESIS
    JUNG, ME
    HATFIELD, GL
    TETRAHEDRON LETTERS, 1983, 24 (31) : 3175 - 3178
12345