tert-butyl 2-amino-3-(benzo[d]thiazol-2-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate | 1369967-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: tert-butyl 2-amino-3-(benzo[d]thiazol-2-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
• 英文别名: tert-butyl 2-amino-3-(benzo[d]thiazol-2-yl)-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate；tert-butyl 2-amino-3-(1,3-benzothiazol-2-yl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carboxylate
• CAS: 1369967-29-2
• 化学式: C₁₉H₂₁N₃O₂S₂
• 分子量: 387.527
• InChiKey: KOGCTMXDSRRSMS-UHFFFAOYSA-N

物化性质

• 沸点：
  593.3±60.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-amino-3-(benzo[d]thiazol-2-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate 在 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(3-(benzo[d]thiazol-2-yl)-6-isopropyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)acetamide
  参考文献：
  名称：

  [EN] INHIBITORS OF HUMAN APURINIC/APYRIMIDINIC ENDONUCLEASE 1
  [FR] INHIBITEURS D'ENDONUCLÉASE APURINIQUE/APYRIMIDIQUE 1

  摘要：

  本文披露了人类APE1的抑制剂，例如公式(I)所示，其中A、B、X、R2和R3的定义如本文所述，这些抑制剂对治疗APE1介导的疾病或紊乱，如癌症，是有用的。还披露了一种包含药学适宜载体和本发明中至少一种化合物的组合物，一种治疗哺乳动物癌症的方法以及一种增强癌症治疗的方法。

  公开号：

  WO2012148889A1
• 作为产物：
  描述：

  N-叔丁氧羰基-4-哌啶酮 、 2-(4-苯基-1,3-噻唑-2-基)乙腈 在 吗啉 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以24%的产率得到tert-butyl 2-amino-3-(benzo[d]thiazol-2-yl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
  参考文献：
  名称：

  COMPOUNDS FOR THE MODULATION OF MYC ACTIVITY

  摘要：

  本发明提供了式（I）的新化合物及其药用可接受的盐、溶剂合物、水合物、互变异构体、立体异构体、同位素标记衍生物以及其组合物。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（例如乳腺癌、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（例如多囊肾病）、自身炎症性疾病和自身免疫疾病的方法。

  公开号：

  US20190048019A1

文献信息

• [EN] COMPOUNDS FOR THE MODULATION OF MYC ACTIVITY<br/>[FR] COMPOSÉS POUR LA MODULATION DE L'ACTIVITÉ DE MYC
  申请人：SYROS PHARMACEUTICALS INC

  公开号：WO2016197078A1

  公开（公告）日：2016-12-08

  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。
• COMPOUNDS FOR TREATING PROTEIN FOLDING DISORDERS
  申请人：Tait Bradley

  公开号：US20130072473A1

  公开（公告）日：2013-03-21

  The present invention is directed to compounds of Formulae (I), (IIa-IIh), (IIIa-IIIe), (IVa-IVc), (Va-V1), (VIa-VII), (VII), (VIII) and (IX), pharmaceutical compositions thereof and methods of use thereof in the treatment of conditions associated with a dysfunction in proteostasis.

  本发明涉及式(I)、(IIa-IIh)、(IIIa-IIIe)、(IVa-IVc)、(Va-V1)、(VIa-VII)、(VII)、(VIII)和(IX)化合物，以及其制备的药物组合物和治疗与蛋白质稳态失调相关疾病的方法。
• 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。
• Compounds for the modulation of MYC activity
  申请人：Syros Pharmaceuticals, Inc.

  公开号：US11274103B2

  公开（公告）日：2022-03-15

  The present invention provides novel compounds of Formula (I) 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, angiogenesis, inflammatory diseases, fibrosis (e.g., polycystic kidney disease), autoinflammatory diseases, and autoimmune diseases in a subject.

  本发明提供了新颖的式(I)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。
• Synthesis, Biological Evaluation, and Structure–Activity Relationships of a Novel Class of Apurinic/Apyrimidinic Endonuclease 1 Inhibitors
  作者：Ganesha Rai、Vaddadi N. Vyjayanti、Dorjbal Dorjsuren、Anton Simeonov、Ajit Jadhav、David M. Wilson、David J. Maloney

  DOI：10.1021/jm201537d

  日期：2012.4.12

  APE1 is an essential protein that operates in the base excision repair (BER) pathway and is responsible for >= 95% of the total apurinic/apyrimidinic (AP) endonuclease activity in human cells. BER is a major pathway that copes with DNA damage induced by several anticancer agents, including ionizing radiation and temozolomide. Overexpression of APEI and enhanced AP endonuclease activity have been linked to increased resistance of tumor cells to treatment with monofunctional alkylators, implicating inhibition of APEI as a valid strategy for cancer therapy. We report herein the results of a focused medicinal chemistry effort around a novel APEI inhibitor, N-(3-(benzo[d]thiazol-2-yl)-6-isopropyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)acetamide (3). Compound 3 and related analogues exhibit single-digit micromolar activity against the purified APE1 enzyme and comparable activity in HeLa whole cell extract assays and potentiate the cytotoxicity of the alkylating agents methylmethane sulfonate and temozolomide. Moreover, this class of compounds possesses a generally favorable in vitro ADME profile, along with good exposure levels in plasma and brain following intraperitoneal dosing (30 mg/kg body weight) in mice.