ethyl 2-acetamidobenzo[d]thiazole-6-carboxylate | 134949-41-0

• 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: ethyl 2-acetamidobenzo[d]thiazole-6-carboxylate
• 英文别名: 2-acetylamino-benzothiazole-6-carboxylic acid ethyl ester；2-Acetylamino-benzothiazol-6-carbonsaeure-aethylester；Ethyl-2-acetamido-benzothiazole-6-carboxylate；ethyl 2-acetamido-1,3-benzothiazole-6-carboxylate
• CAS: 134949-41-0
• 化学式: C₁₂H₁₂N₂O₃S
• mdl: MFCD00441165
• 分子量: 264.305
• InChiKey: QAJGZBLGLSUJGX-UHFFFAOYSA-N

物化性质

• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetamidobenzo[d]thiazole-6-carboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(6-(hydrazinecarbonyl)benzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  Structure-based optimization of oxadiazole-based GSK-3 inhibitors

  摘要：

  Inhibition of glycogen synthase kinase-3 (GSK-3) induces neuroprotective effects, e.g. decreases beta-amyloid production and reduces tau hyperphosphorylation, which are both associated with Alzheimer's disease (AD). The two isoforms of GSK-3 in mammalians are GSK-3 alpha and beta, which share 98% homology in their catalytic domains. We investigated GSK-3 inhibitors based on 2 different scaffolds in order to elucidate the demands of the ATP-binding pocket [1]. Particularly, the oxadiazole scaffold provided potent and selective GSK-3 inhibitors. For example, the most potent inhibitor of the present series, the acetamide 26d, is characterized by an IC50 of 2 nM for GSK-3 alpha and 17 nM for GSK-3 beta. In addition, the benzodioxane 8g showed up to 27-fold selectivity for GSK-3 alpha over GSK-3 beta, with an IC50 of 35 nM for GSK-3 alpha. Two GSK-3 inhibitors were further profiled for efficacy and toxicity in the wild-type (wt) zebrafish embryo assay to evaluate simultaneously permeability and safety. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.006
• 作为产物：
  描述：

  2-氨基苯并噻唑-6-羧酸乙酯 生成 ethyl 2-acetamidobenzo[d]thiazole-6-carboxylate
  参考文献：
  名称：

  Takatori; Nishida, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1950, vol. 70, p. 271,276

  摘要：

  DOI：

文献信息

• Benzothiazole protein trosine kinase inhibitors
  申请人：——

  公开号：US20020123484A1

  公开（公告）日：2002-09-05

  Novel benzothiazoles and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of protein tyrosine kinase-associated disorders such as immunologic disorders.

  新型苯并噻唑及其盐，含有这类化合物的药物组合物，以及使用这类化合物治疗蛋白酪氨酸激酶相关疾病（如免疫性疾病）的方法。
• [EN] BENZOTHIAZOLE PROTEIN TYROSINE KINASE INHIBITORS<br/>[FR] COMPOSES DE BENZOTHIAZOLE UTILISES COMME INHIBITEURS DE LA PROTEINE TYROSINE-KINASE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：WO1999024035A1

  公开（公告）日：1999-05-20

  (EN) Novel benzothiazoles and salts thereof, pharmaceutical compositions containing such compounds, and methods of using such compounds in the treatment of protein tyrosine kinase-associated disorders such as immunologic disorders.(FR) L'invention concerne de nouveaux composés de benzothiazole et des sels desdits composés, des compositions pharmaceutiques contenant ces composés, et des procédés mettant en oeuvre ces composés pour le traitement d'affections, telles que la réaction d'hypersensibilité immédiate, associées à la protéine tyrosine-kinase.

  (中) 本发明涉及新型苯并噻唑化合物及其盐、含有这些化合物的制药组合物，以及使用这些化合物治疗蛋白酪氨酸激酶相关疾病，如免疫疾病的方法。
• Design and Synthesis of Novel 2‐Acetamido, 6‐Carboxamide Substituted Benzothiazoles as Potential BRAFV600E Inhibitors – <i>In vitro</i> Evaluation of their Antiproliferative Activity
  作者：Yakinthi Batsi、Georgia Antonopoulou、Theano Fotopoulou、Kassandra Koumaki、Eftichia Kritsi、Constantinos Potamitis、Maria Goulielmaki、Salomi Skarmalioraki、Chara Papalouka、Eleni Poulou‐Sidiropoulou、Vivian Kosmidou、Stavroula Douna、Maria‐Sofia Vidali、Eleni‐Fani Gkotsi、Aristotelis Chatziioannou、Vassilis L. Souliotis、Vasiliki Pletsa、Olga Papadodima、Vassilis Zoumpourlis、Panagiotis Georgiadis、Maria Zervou、Alexander Pintzas、Ioannis D. Kostas

  DOI：10.1002/cmdc.202300322

  日期：2023.11.16

  Eleven new substituted benzothiazole derivatives were designed and synthesized in order to provide efficient inhibitors of the oncogenic BRAFV600E kinase. They were biologically evaluated as potential BRAFV600E inhibitors, MEK-ERK pathway inhibitors and antiproliferative agents in several colorectal cancer and melanoma cell lines. In all assays applied, the analog 2-acetamido-N-[3-(pyridin-2-ylami

  设计并合成了11 种新的取代苯并噻唑衍生物，以提供致癌 BRAFV600E 激酶的有效抑制剂。它们在多种结直肠癌和黑色素瘤细胞系中被生物学评估为潜在的 BRAFV600E 抑制剂、MEK-ERK 通路抑制剂和抗增殖剂。在所有应用的测定中，类似物2-乙酰氨基-N- [3-(吡啶-2-基氨基)丙基]苯并[d]噻唑-6-甲酰胺( 22 )鉴于其在药物开发中的用途提供了有希望的结果。
• Naim, S Shawkat; Singh, Sudhir K; Sharma, Satyavan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 5, p. 494 - 498
  作者：Naim, S Shawkat、Singh, Sudhir K、Sharma, Satyavan

  DOI：——

  日期：——
• BENZOTHIAZOLE PROTEIN TYROSINE KINASE INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1037632A1

  公开（公告）日：2000-09-27