3-hydroxymethylimidazo[5,1-b]thiazole | 183066-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-hydroxymethylimidazo[5,1-b]thiazole
• 英文别名: 3-(hydroxymethyl)imidazo[5,1-b]thiazole；imidazo[5,1-b][1,3]thiazol-3-ylmethanol
• CAS: 183066-10-6
• 化学式: C₆H₆N₂OS
• 分子量: 154.192
• InChiKey: GGAIHFLAFATQRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxymethylimidazo[5,1-b]thiazole 在 manganese dioxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以to give 0.146 g (yield 71%) of the title compound的产率得到Imidazo[5,1-b]thiazole-3-carbaldehyde
  参考文献：
  名称：

  Cephem derivatives

  摘要：

  本文揭示了一种具有抗菌活性的化合物，其化学式为(I)，其中该化合物在头孢环上的3位具有.beta.-(取代或未取代的咪唑\x9b5,1-b!噻唑基)乙烯基团，同时还具有其盐和酯。该化合物对广泛的细菌谱具有抗菌活性，并且对革兰氏阳性菌、革兰氏阴性菌和耐药菌具有强效的抗菌活性。其中，X代表CH或N，R.sup.1代表氢原子或氨基保护基，R.sup.2代表氢原子、C.sub.1-6烷基、C.sub.3-7环烷基或羟基保护基，R.sup.3不存在或代表氢原子、形成盐的阳离子或羧基保护基，R.sup.4、R.sup.5和R.sup.6可以相同也可以不同，分别独立地代表氢原子或C.sub.1-6烷基，R.sup.7+不存在或代表C.sub.1-6烷基的阳离子，n是0到1的整数。

  公开号：

  US05883089A1
• 作为产物：
  描述：

  ethyl 2-(formylamino)methylthiazole-4-carboxylate 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-hydroxymethylimidazo[5,1-b]thiazole
  参考文献：
  名称：

  CP0569, A New Broad-Spectrum Injectable Carbapenem. Part 1: Synthesis and Structure–Activity Relationships

  摘要：

  A series of 10-methylcarbapenems bearing an (imidazo[5,1-b]thiazolium-6-yl)methyl moiety, a 5,5-fused heterobicycle, at the C-2 position was synthesized and evaluated for in vitro antibacterial activities. CP0569 (1r) and its analogues showed potent antibacterial activities against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), and Gram-negative bacteria, including Pseudomonas aeruginosa. Moreover, CP0569 (1r) exhibited stronger antibacterial activity against MRSA and higher resistance to renal dehydropeptidase-1 (DHP-1) than any currently marketed carbapenems, that is, imipenem (IPM), panipenem (PAPM), and meropenem (MEPM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00304-3

文献信息

• Carbapenem derivatives
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：US06458780B1

  公开（公告）日：2002-10-01

  Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the carbapenem ring have high anti-microbial activities against &bgr;-lactamase producing bacteria, MRSA, resistant-Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities to DHP-1. According to the present invention, there is provided a compound represented by the formula (I), or a pharmacologically acceptable salt thereof or an ester at the 3-position on the carbapenem ring thereof:

  公开了一种新的碳青霉烯衍生物，其在碳青霉烯环的2位置具有取代的咪唑[5,1-b]噻唑基团，对产生β-内酰胺酶的细菌、耐甲氧西林金黄色葡萄球菌(MRSA)、抗假单胞菌属铜绿假单胞菌、肺炎链球菌(PRSP)、肠球菌和流感具有高的抗菌活性，并对DHP-1具有高稳定性。根据本发明，提供了一种由公式(I)表示的化合物，或其药理上可接受的盐，或其碳青霉烯环上3位置的酯。
• Novel carbapenem derivatives
  申请人：——

  公开号：US20030149016A1

  公开（公告）日：2003-08-07

  Disclosed is a novel carbapenem derivative having a substituted imidazo[5,1-b]thiazole group at the 2-position on the, carbapenem ring have high anti-microbial activities against &bgr;-lactamase producing bacteria, MRSA, resistant- Pseudomonas aeruginosa , PRSP, enterococci, and influenza, and high stabilities to DHP-1. According to the present invention, there is provided a compound represented by the formula (I), or a pharmacologically acceptable salt thereof or an ester at the 3-position on the carbapenem ring thereof: 1

  本发明公开了一种新型碳青霉烯衍生物，其在碳青霉烯环上的2位上具有取代咪唑[5,1-b]噻唑基团，对β-内酰胺酶产生的细菌、MRSA、耐药性假单胞菌、PRSP、肠球菌和流感病毒具有高抗菌活性，并对DHP-1具有高稳定性。根据本发明，提供了由式(I)表示的化合物，或其在碳青霉烯环上的3位处的药理学上可接受的盐或酯：1。
• NOVEL CEPHEM DERIVATIVE
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0669336A1

  公开（公告）日：1995-08-30

  A compound represented by general formula (I), i.e., a cephem derivative having an (un)substituted imidazo-[5,1-b]thiazolium-6-yl group at the 3-position of the ring, wherein X represents CH or N; R1 represents H, alkyl, alkenyl, etc.; and R2, R3, R4 and R5 represent each H, alkyl, carbamoyl, amino, etc. This compound has an excellent antibacterial activity and is useful as a remedy for various types of microbism.

  一种由通式（I）代表的化合物，即在环的 3 位上具有一个（未）取代的咪唑并[5,1-b]噻唑鎓-6-基团的头孢衍生物，其中 X 代表 CH 或 N；R1 代表 H、烷基、烯基等；R2、R3、R4 和 R5 分别代表 H、烷基、氨基甲酰基、氨基等。这种化合物具有极佳的抗菌活性，可用于治疗各种微生物。
• NOVEL CARBAPENEM DERIVATIVES
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0760370A1

  公开（公告）日：1997-03-05

  Novel carbapenem derivatives, represented by the following formula (I), having a substituted or unsubstituted imidazo[5,1-b]thiazolium-6-ylmethyl group at the 2-position are disclosed. The compounds represented by the formula (I) have potent antibacterial activity against a wide spectrum of bacteria from Gram-positive bacteria to Gram-negative bacteria including Pseudomonas aeruginosa and, in addition, have potent antibacterial activity against various β-lactamase-producing bacteria and MRSA and are very stable against DHP-1.

  本发明公开了由下式(I)表示的新型碳青霉烯类衍生物，其 2-位具有取代或未取代的咪唑并[5,1-b]噻唑鎓-6-基甲基。由式（I）代表的化合物对从革兰氏阳性菌到革兰氏阴性菌（包括铜绿假单胞菌）在内的广谱细菌具有强效抗菌活性，此外，还对各种产β-内酰胺酶细菌和 MRSA 具有强效抗菌活性，并且对 DHP-1 非常稳定。
• CP6679, a new injectable cephalosporin. Part1: Synthesis and structure–activity relationships
  作者：Masaki Tsushima、Katsuyoshi Iwamatsu、Eijiro Umemura、Toshiaki Kudo、Yasuo Sato、Sojiro Shiokawa、Hiromasa Takizawa、Yuko Kano、Kazuko Kobayashi、Takashi Ida

  DOI：10.1016/s0968-0896(00)00214-5

  日期：2000.12

  A series of cephalosporins bearing a 5,5-fused ring system, an (imidazo/[5,1 -b]thiazolium-6-yl)methyl group, at the C-3 position were synthesized and evaluated for in vitro antibacterial activities. CP6679 (Is) and its analogues showed potent antibacterial activities against Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa. They were also highly active against methicillin-resistant Staphylococcus aureus (MRSA). CP6679 (Is) showed more potent antibacterial activity than ceftazidime (CAZ) or cefpirome (CPR) against Pseudomonas aeruginosa and MRSA. (C) 2000 Elsevier Science Ltd. All rights reserved.