tert-butyl 5-ethynylthiazol-2-ylcarbamate | 1056942-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 5-ethynylthiazol-2-ylcarbamate
• 英文别名: tert-butyl (5-ethynyl-1,3-thiazol-2-yl)carbamate；boc-5-ethynylthiazol-2-amine；(5-ethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester；Tert-butyl (5-ethynylthiazol-2-yl)carbamate；tert-butyl N-(5-ethynyl-1,3-thiazol-2-yl)carbamate
• CAS: 1056942-45-0
• 化学式: C₁₀H₁₂N₂O₂S
• 分子量: 224.283
• InChiKey: CNTJFZSVGGRYNF-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-ethynylthiazol-2-ylcarbamate 在 copper(I) oxide 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 N-[2-[4-[6-[[5-[1-(2-chloro-6-methylphenyl)triazol-4-yl]-1,3-thiazol-2-yl]amino]-2-methylpyrimidin-4-yl]piperazin-1-yl]ethyl]prop-2-enamide
  参考文献：
  名称：

  Design and synthesis of novel dasatinib derivatives as inhibitors of leukemia stem cells

  摘要：

  We used the concept of bioisosteres to design and synthesize a novel series of dasatinib derivatives for the treatment of leukemia. Unfortunately, most of the dasatinib derivatives did not show appreciable inhibition against leukemia cell lines K562 and HL60. However, acrylamide compound 2c had comparable inhibitory activity with dasatinib against K562 cells (IC50 = 0.039 nM vs. 0.069 nM). And amide compound 2a and acrylamide compound 2c also had comparable inhibitory activity with dasatinib against the leukemia cell line HL60 (IC50 = 0.25 nM and 0.26 nM vs. 0.11 nM). Against the leukemia progenitor cell line KG1a, triazole compounds 15a and 15d-15f and oxadiazole compounds 24a-24d were more potent than dasatinib. In particular, the hydroxyl compounds 15a and 24a were about 64 and 180 fold more potent than dasatinib against KG1a cells (IC50 = 0.14 mu M and 0.05 mu M vs. 8.98 mu M). Compounds 15a and 24a also inhibited colony formation in MCF-7 cells and inhibited cell migration in the cell wound scratch assay in B16BL6 cells. Moreover, hydroxyl compounds 15a and 24a had low toxicity in vivo. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.01.011
• 作为产物：
  描述：

  N-BOC-2-氨基-5-溴噻唑 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 tert-butyl 5-ethynylthiazol-2-ylcarbamate
  参考文献：
  名称：

  WO2008/154642

  摘要：

  公开号：

文献信息

• ACETAMIDE DERIVATIVES AS GLUCOKINASE ACTIVATORS, THEIR PROCESS AND MEDICINAL APPLICATION
  申请人：Bhuniya Debnath

  公开号：US20100310493A1

  公开（公告）日：2010-12-09

  Acetamide derivatives, their stereoisomers, tautomers, prodrugs, pharmaceutically acceptable salts, polymorphs, solvates and formulations thereof for the prophylaxis, management, treatment, control of progression, or adjunct treatment of diseases and/or medical conditions where the activation of glucokinase would be beneficial, are disclosed. The disclosure also provides process of preparation of these acetamide derivatives.

  乙酰胺衍生物，它们的立体异构体、互变异构体、前药、药用可接受盐、多型体、溶剂合物及其配方，用于预防、管理、治疗、控制疾病和/或医疗状况的进展，或者作为激活葡萄糖激酶有益时的辅助治疗，已被披露。该披露还提供了这些乙酰胺衍生物的制备方法。
• 噻唑杂环类化合物及其制备方法和应用
  申请人：天津国际生物医药联合研究院

  公开号：CN106279143A

  公开（公告）日：2017-01-04

  本发明提供了噻唑杂环类化合物及其制备方法和应用，其中，噻唑杂环类化合物具有以下结构通式：通过细胞水平实验发现，本发明提供的噻唑杂环类化合物均可以抑制K562、HL60、KG1a细胞的增殖，特别是实例3化合物(化合物4c)在药物浓度低于阳性对照药物达沙替尼的情况下，可以同样实现抑制K562、HL60、KG1a细胞增殖的效果，因此本发明提供的噻唑杂环类化合物可以用于治疗白血病。
• [EN] AMINOTHIAZOLE COMPOUNDS AS C-KIT INHIBITORS<br/>[FR] COMPOSÉS D'AMINOTHIAZOLE EN TANT QU'INHIBITEURS DE C-KIT
  申请人：ARIAD PHARMA INC

  公开号：WO2018112136A1

  公开（公告）日：2018-06-21

  The invention relates to c-Kit inhibitors useful in the treatment of cancers, and other -threonine kinase mediated diseases, having the Formula: (I) wherein A, L, R1, R2, R3, and n are described herein.

  这项发明涉及一种在治疗癌症和其他-threonine激酶介导的疾病中有用的c-Kit抑制剂，其化学式为：(I)，其中A、L、R1、R2、R3和n如本文所述。
• [EN] BICYCLIC ALKYNE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS D'ALCYNES BICYCLIQUES ET LEURS UTILISATIONS
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2015050505A1

  公开（公告）日：2015-04-09

  The present invention relates to certain compounds (e.g., imidazopyrazine, imidazopyridine, imidazopyridazine and imidazpyrimidine compounds) that act as inhibitors of the MAP kinase interacting kinases MNK2a, MNK2b, MNK1a, and MNK1b. The present invention further relates to pharmaceutical compositions comprising these compounds, and to the use of the compounds for the prevention and treatment of diseases (e.g., proliferative diseases (e.g., cancer), inflammatory diseases, autoimmune diseases, metabolic diseases, and neurodegenerative diseases (e.g. autism, autism spectrum disorders, Alzheimer's disease)), as well as methods of treating these diseases

  本发明涉及某些化合物（例如，咪唑吡嗪、咪唑吡啶、咪唑吡嗪和咪唑嘧啶化合物），这些化合物作为MAP激酶相互作用激酶MNK2a、MNK2b、MNK1a和MNK1b的抑制剂。本发明还涉及包含这些化合物的药物组合物，以及利用这些化合物预防和治疗疾病（例如，增殖性疾病（例如癌症）、炎症性疾病、自身免疫性疾病、代谢性疾病和神经退行性疾病（例如自闭症、自闭症谱系障碍、阿尔茨海默病））的用途，以及治疗这些疾病的方法。
• ANTIBACTERIAL AGENTS
  申请人：Moser Heinz E.

  公开号：US20100190766A1

  公开（公告）日：2010-07-29

  Antibacterial compounds of formula (I) are provided: as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

  提供化学式(I)的抗菌化合物：以及其立体异构体，药学上可接受的盐，酯和前药；包含这些化合物的制药组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。