3-甲基咪唑并[2,1-b][1,3]噻唑-6-羧酸 | 57332-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 中文名称: 3-甲基咪唑并[2,1-b][1,3]噻唑-6-羧酸
• 英文名称: ethyl 3-methylimidazo<2,1-b>thiazole-6-carboxylate
• 英文别名: ethyl 3-methylimidazo[2,1-b]thiazole-6-carboxylate；3-methyl-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester；3-methyl-imidazo-thiazole-6-carboxylic acid ethyl ester；3-methyl-imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester；3-methyl-6-carboethoxy-imidazo-(2,1-b)thiazole；3-methyl-6-carboethoxy-imidazo(2,1-b)thiazole；ethyl 3-methylimidazo[2,1-b][1,3]thiazole-6-carboxylate
• CAS: 57332-95-3
• 化学式: C₉H₁₀N₂O₂S
• 分子量: 210.257
• InChiKey: PHRNIFUPIWVNOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲基咪唑并[2,1-b][1,3]噻唑-6-羧酸 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以5%的产率得到3-methylimidazo<2,1-b>thiazole-6-carboxylic acid
  参考文献：
  名称：

  Abignente; Arena; de Caprariis, Farmaco, Edizione Scientifica, 1981, vol. 36, # 10, p. 893 - 904

  摘要：

  DOI：
• 作为产物：
  描述：

  4-乙氧基羰基咪唑-2-硫醇 、 一氯丙酮 在 三氯氧磷 、 sodium carbonate 作用下， 以 乙醇 、 乙腈 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 3-甲基咪唑并[2,1-b][1,3]噻唑-6-羧酸
  参考文献：
  名称：

  3-AZA-BICYCLO[3.1.0]HEXANE DERIVATIVES

  摘要：

  这项发明涉及式(I)的3-aza-双环[3.1.0]己烷衍生物，其中A、B、n、X和R1如描述中所述，以及其盐，以及它们作为促进睡眠的荷尔蒙受体拮抗剂的用途。

  公开号：

  US20100016401A1

文献信息

• Imidazo(2,1-B)thiazoles
  申请人：Plantex Ltd.

  公开号：US04267339A1

  公开（公告）日：1981-05-12

  There are disclosed certain novel imidazo(2,1-b)thiazoles, their physiologically acceptable acid addition--or quaternary ammonium salts and a process for their preparation. Said compounds show a good anti-diabetic activity.

  本发明涉及一种新型咪唑（2,1-b）噻唑的化合物，以及它们的生理上可接受的酸加成物或季铵盐，以及其制备方法。所述化合物表现出良好的抗糖尿病活性。
• Pharmaceutical compositions containing imidazo(2,1-b)thiazoles and
  申请人：Plantex, Ltd.

  公开号：US04137320A1

  公开（公告）日：1979-01-30

  Pharmaceutical compositions containing certain imidazo(2,1-b)thiazoles, their physiologically acceptable acid addition- or quaternary ammonium salts, and a process for reducing blood sugar levels by the administration thereof.

  含有特定咪唑(2,1-b)噻唑类化合物的药物组合物，其生理上可接受的酸加成物或季铵盐，以及通过其管理来降低血糖水平的过程。
• Discovery of Imidazo[2,1-<i>b</i>]thiazole HCV NS4B Inhibitors Exhibiting Synergistic Effect with Other Direct-Acting Antiviral Agents
  作者：Ning-Yu Wang、Ying Xu、Wei-Qiong Zuo、Kun-Jie Xiao、Li Liu、Xiu-Xiu Zeng、Xin-Yu You、Li-Dan Zhang、Chao Gao、Zhi-Hao Liu、Ting-Hong Ye、Yong Xia、Ying Xiong、Xue-Jiao Song、Qian Lei、Cui-Ting Peng、Hong Tang、Sheng-Yong Yang、Yu-Quan Wei、Luo-Ting Yu

  DOI：10.1021/jm501934n

  日期：2015.3.26

  The design, synthesis, and SAR studies of novel inhibitors of HCV NS4B based on the imidazo[2,1-b]thiazole scaffold were described. Optimization of potency with respect to genotype 1b resulted in the discovery of two potent leads 26f (EC50 = 16 nM) and 28g (EC50 = 31 nM). The resistance profile studies revealed that 26f and 28g targeted HCV NS4B, more precisely the second amphipathic alpha helix of NS4B (4BAH2). Cross-resistance between our 4BAH2 inhibitors and other direct-acting antiviral agents targeting NS3/4A, NS5A, and NS5B was not observed. For the first time, the synergism of a series of combinations based on 4BAH2 inhibitors was evaluated. The results demonstrated that our 4BAH2 inhibitor 26f was synergistic with NS3/4A inhibitor simeprevir, NS5A inhibitor daclatasvir, and NS5B inhibitor sofosbuvir, and it could also reduce the dose of these drugs at almost all effect levels. Our study suggested that favorable effects could be achieved by combining 4BAH2 inhibitors such as 26f with these approved drugs and that new all-oral antiviral combinations based on 4BAH2 inhibitors were worth developing to supplement or even replace current treatment regimens for curing HCV infection.
• Abignente; Arena; Carola, Farmaco, Edizione Scientifica, 1979, vol. 34, # 5, p. 417 - 432
  作者：Abignente、Arena、Carola、de Caprariis、Caputi、Rossi、Giordano、Vacca、Lampa、Marmo

  DOI：——

  日期：——
• ABIGNENTE, E.;ARENA, F.;DE, CAPRARIIS, P.;FERRERI, C.;MARMO, E.;OTTAVO, R+, FARMACO. ED. SCI., 1981, 36, N 10, 893-904
  作者：ABIGNENTE, E.、ARENA, F.、DE, CAPRARIIS, P.、FERRERI, C.、MARMO, E.、OTTAVO, R+

  DOI：——

  日期：——