Synthesis and antibacterial activities of new piperidine substituted (5R)-[1,2,3]triazolylmethyl and (5R)-[(4-F-[1,2,3]triazolyl)methyl]oxazolidinones

被引：15

作者：

Shin, Hyo-Nim ^{[1
]}

Seo, Seon Hee ^{[1
]}

Choo, Hyunah ^{[1
]}

Kuem, Gyochang ^{[1
]}

Choi, Kyung Il ^{[1
]}

Nam, Ghilsoo ^{[1
]}

机构：

[1] Korea Inst Sci & Technol, Brain Sci Inst, Ctr Neuromed, Seoul 136791, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 05期

关键词：

Oxazolidinone; Antibiotics; Synthesis; Antibacterial activity; IN-VITRO ACTIVITY; IDENTIFICATION;

D O I：

10.1016/j.bmcl.2013.01.033

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel series of 5(R)-[1,2,3]triazolylmethyl and (5R)-[(4-F-[1,2,3]triazolyl)methyl]oxazolidinones having various piperidine group were synthesized and evaluated antibacterial activity against clinically isolated resistant strains of Gram-positive and Gram-negative bacteria. The compound 12a having exo-cyanoethylidene group in the 4-position of piperidine ring was found to be two to threefold more potent than the linezolid against penicillin-resistant Staphylococcus pneumonia and Staphylococcus agalactiae, and also exhibited reduced MAO-B inhibitory activity. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1193 / 1196

页数：4

共 50 条

[1] (2S,4R,5R)-(-)-3-ISOPROPYL-4-METHYL-5-PHENYL-1,2,3-OXATHIAZOLIDINE 2-OXIDE
ROBINSON, PD
HUA, DH
CHEN, JS
LAGNEAU, N
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 : 1372 - 1374
[2] Synthesis and antibacterial activities of N-substituted-glycinyl 1H-1,2,3-triazolyl oxazolidinones
Phillips, Oludotun A.
Udo, Edet E.
Abdel-Hamid, Mohammed E.
Varghese, Reny
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 66 : 246 - 257
[3] Diastereoselective total synthesis of piperidine alkaloids: (2R,5R)-5-hydroxyhomopipecolic acid and (2R,5R,8R)-5-hydroxysedamine
Khobare, Sandip R.
Gajare, Vikas S.
Rajana, Nagaraju
Datrika, Rajender
Reddy, K. Srinivasa
Kumar, U. K. Syam
Siddaiah, Vidavalur
TETRAHEDRON LETTERS, 2015, 56 (17) : 2207 - 2210
[4] Modified synthesis of methyl (1R,2R,3E,5R)-3-(hydroxyimino)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxylate from (R)-4-menthen-3-one
G. Yu. Ishmuratov
A. V. Bannova
E. R. Latypova
R. R. Muslukhov
A. A. Smol′nikov
R. F. Talipov
Chemistry of Natural Compounds, 2012, 48 : 789 - 790
[5] Modified synthesis of methyl (1R,2R,3E,5R)-3-(hydroxyimino)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxylate from (R)-4-menthen-3-one
Ishmuratov, G. Yu.
Bannova, A. V.
Latypova, E. R.
Muslukhov, R. R.
Smol'nikov, A. A.
Talipov, R. F.
CHEMISTRY OF NATURAL COMPOUNDS, 2012, 48 (05) : 789 - 790
[6] (2S, 3S, 5R)-diphenylmethyl 4,4-dioxo-3(1,2,3-triazol-1-ylmethyl)-2-penicillanate
Bai, Guo-Yi
Peng, Hong-Wei
Qin, Xin-Ying
Zhang, Yue-Cheng
Zeng, Tao
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O4997 - O4998
[7] A(1R,2R,5R)-(+)-2α-hydroxypinan-3-one ketimine
Ayers, JT
Sonar, VN
Parkin, S
Dwoskin, LP
Crooks, PA
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2682 - O2684
[8] Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole) methyl oxazolidinones
Phillips, Oludotun A.
Udo, Edet E.
Abdel-Hamid, Mohammed E.
Varghese, Reny
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (08) : 3217 - 3227
[9] Crystal structure of (2R,3R,5R)-5-(1-iodo-1-methylethyl)-3-(5-(1R,2R,5R)-5-(1-iodo-1-methylethyl)-2-methyl-3-oxocyclohexyl)-2-furyl)-2-methyl-cyclohexan-1-one, C24H34O3I2
Peters, K
Peters, EM
Olioso, B
De Lucchi, O
Fabris, F
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 1998, 213 (02): : 255 - 256
[10] Synthesis of 4-R-3-(4-R1-5-R2-1,2,3-triazolyl-1)furazans.: 1.: Azido-furazans in reaction of 1,3-dipolar cycloaddition to substituted acetylenes
Batog, LV
Konstantinova, LS
Rozhkov, VY
Strelenko, YA
Lebedev, OV
Khmel'nitskii, LI
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (01): : 100 - 110

← 1 2 3 4 5 →