5-乙炔基-1,3-噻唑-2-胺 | 912639-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-乙炔基-1,3-噻唑-2-胺
• 英文名称: 2-amino-5-ethynylthiazole
• 英文别名: 5-Ethynylthiazol-2-amine；5-ethynyl-1,3-thiazol-2-amine
• CAS: 912639-82-8
• 化学式: C₅H₄N₂S
• 分子量: 124.166
• InChiKey: ZOANNWMYAULKAT-UHFFFAOYSA-N

物化性质

• 沸点：
  266.6±13.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-碘-4-甲基-N-[4-[(4-甲基-1-哌嗪基)甲基]-3-(三氟甲基)苯基]苯甲酰胺 、 5-乙炔基-1,3-噻唑-2-胺 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-((2-aminothiazol-5-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide
  参考文献：
  名称：

  Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR–ABL including the T315I gatekeeper mutant

  摘要：

  Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.060
• 作为产物：
  描述：

  5-(2-trimethylsilylethynyl)-1,3-thiazol-2-amine 在 甲醇 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 5-乙炔基-1,3-噻唑-2-胺
  参考文献：
  名称：

  Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR–ABL including the T315I gatekeeper mutant

  摘要：

  Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.060

文献信息

• 2-Thioethenyl substituted carbapenem derivatives
  申请人：Maruyama Takahisa

  公开号：US20070004700A1

  公开（公告）日：2007-01-04

  [Objective] An objective of the present invention is to provide compounds that are effective against various resistant bacteria which cause current clinical problems, for example, pneumococci including penicillin resistant Streptococcus pneumoneae (PRSP), Haemophilus influenzae including bata-lactamase-nonproducing ampicillin-resistant Haemophilus influenzae (BLNAR), and Moraxella ( Branhamella ) catarrhalis. [Structure] The present invention provides 2-ethenylthio-based carbapenem derivatives represented by the formula (I) or pharmaceutically acceptable salts thereof that are effective, for example, against pneumococci including penicillin resistant Streptococcus pneumoneae (PRSP), Haemophilus influenzae including beta-lactamase-nonproducing ampicillin-resistant Haemophilus influenzae (BLNAR), and Moraxella (Branhamella) catarrhalis:

  本发明的一个目标是提供对抗引起当前临床问题的各种耐药细菌有效的化合物，例如对抗青霉素耐药的肺炎球菌（PRSP）、包括产β-内酰胺酶非产生性氨苄青霉素耐药的流感嗜血杆菌（BLNAR）和喜马拉雅链球菌（布兰氏链球菌）等。本发明提供了以公式（I）表示的基于2-乙烯硫的碳青霉烯衍生物或其药用可接受盐，例如对抗青霉素耐药的肺炎球菌（PRSP）、包括产β-内酰胺酶非产生性氨苄青霉素耐药的流感嗜血杆菌（BLNAR）和喜马拉雅链球菌（布兰氏链球菌）有效。
• Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR–ABL including the T315I gatekeeper mutant
  作者：Mathew Thomas、Wei-Sheng Huang、David Wen、Xiaotian Zhu、Yihan Wang、Chester A. Metcalf、Shuangying Liu、Ingrid Chen、Jan Romero、Dong Zou、Raji Sundaramoorthi、Feng Li、Jiwei Qi、Lisi Cai、Tianjun Zhou、Lois Commodore、Qihong Xu、Jeff Keats、Frank Wang、Scott Wardwell、Yaoyu Ning、Joseph T. Snodgrass、Marc I. Broudy、Karin Russian、John Iuliucci、Victor M. Rivera、Tomi K. Sawyer、David C. Dalgarno、Tim Clackson、William C. Shakespeare

  DOI：10.1016/j.bmcl.2011.04.060

  日期：2011.6

  Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML. (C) 2011 Elsevier Ltd. All rights reserved.