(R)-benzyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate | 1364666-98-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-benzyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate
• 英文别名: benzyl (4R)-2-phenyl-4,5-dihydrothiazole-4-carboxylate；benzyl (4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylate
• CAS: 1364666-98-7
• 化学式: C₁₇H₁₅NO₂S
• 分子量: 297.378
• InChiKey: FEAZCOHGPPYHDN-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-benzyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate 在 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到benzyl 2-phenylthiazole-4-carboxylate
  参考文献：
  名称：

  Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds

  摘要：

  Tuberculosis (TB) is a devastating disease resulting in a death every 20 s. Thus, new drugs are urgently needed. Herein we report ten classes of compounds-oxazoline, oxazole, thiazoline, thiazole, pyrazole, pyridine, isoxazole,imidazo[1,2-a] pyridine, imidazo[1,2-a] pyrimidine and imidazo[1,2-c] pyrimidine-which have good (micromolar) to excellent (sub-micromolar) antitubercular potency. The 5,6-fused heteroaromatic compounds were the most potent with MIC's as low as < 0.195 mu M (9 and 11). Overall, the imidazo[1,2-a] pyridine class was determined to be most promising, with potency similar to isoniazid and PA-824 against replicating Mtb H(37)Rv, clinically relevant drug sensitive, multi-and extensively resistant Mtb strains as well as having good in vitro metabolic stability. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.025
• 作为产物：
  描述：

  苯甲腈 在 4-二甲氨基吡啶 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.0h， 生成 (R)-benzyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate
  参考文献：
  名称：

  Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds

  摘要：

  Tuberculosis (TB) is a devastating disease resulting in a death every 20 s. Thus, new drugs are urgently needed. Herein we report ten classes of compounds-oxazoline, oxazole, thiazoline, thiazole, pyrazole, pyridine, isoxazole,imidazo[1,2-a] pyridine, imidazo[1,2-a] pyrimidine and imidazo[1,2-c] pyrimidine-which have good (micromolar) to excellent (sub-micromolar) antitubercular potency. The 5,6-fused heteroaromatic compounds were the most potent with MIC's as low as < 0.195 mu M (9 and 11). Overall, the imidazo[1,2-a] pyridine class was determined to be most promising, with potency similar to isoniazid and PA-824 against replicating Mtb H(37)Rv, clinically relevant drug sensitive, multi-and extensively resistant Mtb strains as well as having good in vitro metabolic stability. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.025

文献信息

• Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds
  作者：Garrett C. Moraski、Lowell D. Markley、Mayland Chang、Sanghyun Cho、Scott G. Franzblau、Chang Hwa Hwang、Helena Boshoff、Marvin J. Miller

  DOI：10.1016/j.bmc.2012.02.025

  日期：2012.4

  Tuberculosis (TB) is a devastating disease resulting in a death every 20 s. Thus, new drugs are urgently needed. Herein we report ten classes of compounds-oxazoline, oxazole, thiazoline, thiazole, pyrazole, pyridine, isoxazole,imidazo[1,2-a] pyridine, imidazo[1,2-a] pyrimidine and imidazo[1,2-c] pyrimidine-which have good (micromolar) to excellent (sub-micromolar) antitubercular potency. The 5,6-fused heteroaromatic compounds were the most potent with MIC's as low as < 0.195 mu M (9 and 11). Overall, the imidazo[1,2-a] pyridine class was determined to be most promising, with potency similar to isoniazid and PA-824 against replicating Mtb H(37)Rv, clinically relevant drug sensitive, multi-and extensively resistant Mtb strains as well as having good in vitro metabolic stability. (C) 2012 Elsevier Ltd. All rights reserved.