Synthesis of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-ones and their 2-methylene derivatives as potential spermicidal and microbicidal agents

被引：18

作者：

Pandey, Rishi Ranjan ^{[1
]}

Srivastava, Akansha ^{[1
]}

Malasoni, Richa ^{[1
]}

Naqvi, Arshi ^{[1
]}

Jain, Ashish ^{[2
]}

Maikhuri, Jagdamba Prasad ^{[2
]}

Paliwal, Sarvesh ^{[3
]}

Gupta, Gopal ^{[2
]}

Dwivedi, Anil Kumar ^{[1
]}

机构：

[1] CSIR Cent Drug Res Inst, Div Pharmaceut, Lucknow 226001, Uttar Pradesh, India

[2] CSIR Cent Drug Res Inst, Div Endocrinol, Lucknow 226001, Uttar Pradesh, India

[3] Banasthali Vidyapeeth, Dept Pharm, Banasthali, Rajasthan, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 17期

关键词：

Spermicides; Cinchotoxin derivatives; Microbicides; HeLa cells; Trichomonas vaginalis; IN-VITRO; BENZALKONIUM CHLORIDE; SULFHYDRYL-GROUPS; DISULFIDE ESTERS; SPERM; ACRYLOPHENONES; SPERMATOZOA; SEARCH; VIRUS; ACID;

D O I：

10.1016/j.bmcl.2012.06.062

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of twenty two derivatives of 3-(1-alkyl/aminoalkyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one and their 2-methylene derivatives were synthesized from naturally abundant cinchonine (I). Tartarate salts of these compounds were prepared and evaluated for spermicidal activity. The most active compounds (24, 27, 34, 36, and 38) showing potent spermicidal activity were further evaluated against different strains of Trichomonas vaginalis, for antimicrobial activity, in HeLa cell lines for cytotoxicity and against Lactobacillus jensenii for eco-safety. The tartarate of 3-(1-pentyl-3-vinyl-piperidin-4-yl)-1-(quinolin-4-yl)-propan-1-one (27) was found to be more active than N-9 in spermicidal activity. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5735 / 5738

页数：4

共 50 条

[1] SYNTHESIS AND PHARMACOLOGICAL INVESTIGATION OF NOVEL 1-(4-BENZHYDRYL PIPERAZIN-1-YL)-3-(DI-SUBSTITUTED) PROPAN-1-ONES AS ANTIHISTAMINIC AGENTS
Shakya, Ashok K.
Siddiqui, H. H.
Singh, Kuldeep
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 22 (02) : 99 - 102
[2] Fenbufen based 3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]-1-(biphenyl-4-yl)propan-1-ones as safer antiinflammatory and analgesic agents
Husain, Asif
Ahmad, Ausaf
Alam, M. M.
Ajmal, Mohd.
Ahuja, Priyanka
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (09) : 3798 - 3804
[3] Syntheses and biological evaluation of 18F-labeled 3-(1-benzyl-piperidin-4-yl)-1-(1-methyl-1H-indol-3-yl) propan-1-ones for in vivo mapping of acetylcholinesterase
Choe, YS
Oh, SJ
Shim, I
Naruto, S
Chi, DY
Kim, SE
Lee, KH
Choi, Y
Kim, BT
NUCLEAR MEDICINE AND BIOLOGY, 2000, 27 (03) : 263 - 267
[4] 1-(Piperidin-1-yl)-3-(2,4,6-trimethylphenyl)propan-2-ol
Maharramov, Abel M.
Khalilov, Ali N.
Gurbanov, Atash V.
Allakhverdiev, Mirze A.
Ng, Seik Weng
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O739 - U2851
[5] Synthesis of 1-(4-phenoxyphenyl)-3-[5-(substituted aryl)-1,3,4-oxadiazol-2-yl]propan-1-ones as safer anti-inflammatory and analgesic agents
Husain, Asif
Ahmad, F. J.
Ajmal, Mohd
Ahuja, Priyanka
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2008, 73 (8-9) : 781 - 791
[6] Synthesis of 2-(6-substituted quinolin-4-yl)-1-(4-aryl-1H-1,2,3-triazol-1-yl) propan-2-ol as potential antifungal and antitubercular agents
Shinde, Abhijit
Thakare, Prashant P.
Nandurkar, Yogesh
Bhoye, Manish
Chavan, Abhijit
Mhaske, Pravin C.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY REPORTS, 2023, 7
[7] 3-(Benzotriazol-2-yl)-1-(biphenyl-4-yl)propan-1-one
Cheng, Kun
Zhang, Hui-Qing
Tian, Na-Na
Wan, Jun
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3091 - U2473
[8] Synthesis and Antimicrobial Activity of 3-(1-Aryl-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)propan-1-ones
M. Nagamani
Ch. Anjaiah
D. Praveen
P. Jalapathi
Russian Journal of General Chemistry, 2018, 88 : 812 - 814
[9] Synthesis and Antimicrobial Activity of 3-(1-Aryl-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)propan-1-ones
Nagamani, M.
Anjaiah, Ch.
Praveen, D.
Jalapathi, P.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (04) : 812 - 814
[10] N '-{[2-(Piperidin-1-yl)quinolin-3-yl]methylene}pyridine-4-carbohydrazide
Afzal, Obaid
Bawa, Sandhya
Kumar, Suresh
Tonk, Rajiv K.
MOLBANK, 2012, (01)

← 1 2 3 4 5 →