2-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)acetonitrile | 112146-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)acetonitrile
• 英文别名: 2-[5-(Trifluoromethyl)-1,3-benzothiazol-2-yl]acetonitrile
• CAS: 112146-11-9
• 化学式: C₁₀H₅F₃N₂S
• mdl: MFCD02073523
• 分子量: 242.224
• InChiKey: QBZYAWYXEIFDQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)acetonitrile 在 吗啉 、 sulfur 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 tert-butyl 2-acrylamido-3-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
  参考文献：
  名称：

  [EN] COMPOUNDS FOR THE MODULATION OF MYC ACTIVITY
  [FR] COMPOSÉS POUR LA MODULATION DE L'ACTIVITÉ DE MYC

  摘要：

  本发明提供了式（I）和式（II）的新化合物以及药学上可接受的盐、溶剂合物、水合物、互变异构体、立体异构体、同位素标记衍生物及其组合物。还提供了涉及这些化合物或组合物用于治疗或预防增生性疾病的方法和试剂盒，例如癌症（如乳腺癌、前列腺癌、淋巴瘤、肺癌、胰腺癌、卵巢癌、神经母细胞瘤或结肠直肠癌）、良性肿瘤、血管生成、炎症性疾病、纤维化（如多囊肾病）、自身炎症性疾病和自身免疫疾病的方法。

  公开号：

  WO2016197078A1
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 3-氨基-4-碘三氟甲苯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,1'-双(二苯基膦)二茂铁 calcium oxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以92%的产率得到2-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)acetonitrile
  参考文献：
  名称：

  Palladium(0)-catalyzed Synthesis of 2-Alkylbenzothiazoles by a Novel Thiation of 1-Amino-2-iodoarenes with Thioamides

  摘要：

  零价钯催化下，1-氨基-2-碘苯与硫酰胺反应，直接生成2-XCH2取代的苯并噻唑（X=H, CH3, OCH3, CN）。

  DOI：

  10.1246/cl.1987.839

文献信息

• Compounds for the modulation of myc activity
  申请人：Syros Pharmaceuticals, Inc.

  公开号：US10787444B2

  公开（公告）日：2020-09-29

  The present invention provides novel compounds of Formula (I) and Formula (II) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are methods and kits involving the compounds or compositions for treating or preventing proliferative diseases, e.g., cancers (e.g., breast cancer, prostate cancer, lymphoma, lung cancer, pancreatic cancer, ovarian cancer, neuroblastoma, or colorectal cancer), benign neoplasms, angio genesis, inflammatory diseases, fibrosis (e.g., polycystic kidney disease), autoinflammatory diseases, and autoimmune diseases in a subject.

  本发明提供了式(I)和式(II)的新型化合物及其药学上可接受的盐、溶液剂、水合物、同系物、立体异构体、同位素标记的衍生物及其组合物。还提供了涉及这些化合物或组合物的方法和试剂盒，用于治疗或预防增殖性疾病，如癌症（如乳腺癌、前列腺癌、淋巴瘤、肺癌、胰腺癌、卵巢癌、神经母细胞瘤或结肠直肠癌）、良性肿瘤、血管生成、炎症性疾病、纤维化（如多囊肾）、自身炎症性疾病和自身免疫性疾病。
• Novel synthesis of 2-amino-3-hetaryl-4(5H)-oxothiophenes
  作者：Yu. M. Volovenko、T. A. Volovnenko、A. V. Dobrydnev

  DOI：10.1007/s10593-006-0132-0

  日期：2006.5
• Design and Synthesis of the First Generation of Novel Potent, Selective, and in Vivo Active (Benzothiazol-2-yl)acetonitrile Inhibitors of the c-Jun N-Terminal Kinase
  作者：Pascale Gaillard、Isabelle Jeanclaude-Etter、Vittoria Ardissone、Steve Arkinstall、Yves Cambet、Montserrat Camps、Christian Chabert、Dennis Church、Rocco Cirillo、Denise Gretener、Serge Halazy、Anthony Nichols、Cedric Szyndralewiez、Pierre-Alain Vitte、Jean-Pierre Gotteland

  DOI：10.1021/jm0310986

  日期：2005.7.1

  Several lines of evidence support the hypothesis that c-Jun N-terminal kinase (JNKs) plays a critical role in a wide range of diseases including cell death (apoptosis)-related disorders (neurodegenerative diseases, brain, heart, and renal ischemia, epilepsy) and inflammatory disorders (multiple sclerosis, rheumatoid arthritis, inflammatory bowel diseases). Screening of our internal compound collection for inhibitors of JNK3 led to the identification of (benzothiazol-2-yl)acetonitrile derivatives as potent and selective JNK1, -2, -3 inhibitors. Starting from initial hit 1 (AS007149), the chemistry and initial structure-activity relationship (SAR) of this novel and unique kinase inhibitor template were explored. Investigation of the SAR rapidly revealed that the benzothiazol-2-ylacetonitrile pyrimidine core was crucial to retain a good level of potency on rat JNK3. Therefore, compound 6 was further optimized by exploring a number of distal combinations in place of the chlorine atom. This led to the observation that the presence of an aromatic group, two carbons away from the aminopyrimidine moiety and bearing substituents conferring hydrogen bond acceptor (HBA) properties, could improve the potency. Further improvements to the biological and biopharmaceutical profile of the most promising compounds were performed, resulting in the discovery of compound 59 (AS601245). The in vitro and in vivo anti-inflammatory potential of this new JNK inhibitor was investigated and found to demonstrate efficacy per oral route in an experimental model of rheumatoid arthritis (RA).
• Nucleophilic substitution in 1-alkyl-4,5-dichloro-3-nitropyridazin-6-ones
  作者：Yu. M. Volovenko、T. A. Volovnenko

  DOI：10.1007/s10593-006-0115-1

  日期：2006.4
• COMPOUNDS FOR THE MODULATION OF MYC ACTIVITY
  申请人：Roberts Christopher

  公开号：US20180162851A1

  公开（公告）日：2018-06-14

  The present invention provides novel compounds of Formula (I) and Formula (II) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are methods and kits involving the compounds or compositions for treating or preventing proliferative diseases, e.g., cancers (e.g., breast cancer, prostate cancer, lymphoma, lung cancer, pancreatic cancer, ovarian cancer, neuroblastoma, or colorectal cancer), benign neoplasms, angio genesis, inflammatory diseases, fibrosis (e.g., polycystic kidney disease), autoinflammatory diseases, and autoimmune diseases in a subject.