5-溴噻吩-2-羧酸叔丁酯 | 62224-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-溴噻吩-2-羧酸叔丁酯
• 英文名称: tert-butyl 5-bromothiophene-2-carboxylate
• 英文别名: tert-butyl 5-bromo-2-thiophenecarboxylate
• CAS: 62224-20-8
• 化学式: C₉H₁₁BrO₂S
• 分子量: 263.155
• InChiKey: HFPUIDDBBWKTNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-溴噻吩-2-羧酸叔丁酯 在 正丁基锂 、 水 、 羟胺 、 碳酸氢钠 、 溶剂黄146 、 三氟乙酸 、 锌 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 5-((((9H-fluoren-9-yl)methoxy)carbonylamino)methyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Identification of Potent and Selective Small-Molecule Inhibitors of Caspase-3 through the Use of Extended Tethering and Structure-Based Drug Design

  摘要：

  The design, synthesis, and in vitro activities of a series of potent and selective small-molecule inhibitors of caspase-3 are described. From extended tethering, a salicylic acid fragment was identified as having binding affinity for the S-4 pocket of caspase-3. X-ray crystallography and molecular modeling of the initial tethering hit resulted in the synthesis of 4, which reversibly inhibited caspase-3 with a K-i = 40 nM. Further optimization led to the identification of a series of potent and selective inhibitors with K-i values in the 20-50 nM range. One of the most potent compounds in this series, 66b, inhibited caspase-3 with a K-i = 20 nM and selectivity of 8-500-fold for caspase-3 vs a panel of seven caspases (1, 2, and 4-8). A high-resolution X-ray cocrystal structure of 4 and 66b supports the predicted binding modes of our compounds with caspase-3.

  DOI：

  10.1021/jm020230j
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2,3-二甲基-1-丁烯 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 15.0h， 生成 5-溴噻吩-2-羧酸叔丁酯
  参考文献：
  名称：

  Identification of Potent and Selective Small-Molecule Inhibitors of Caspase-3 through the Use of Extended Tethering and Structure-Based Drug Design

  摘要：

  The design, synthesis, and in vitro activities of a series of potent and selective small-molecule inhibitors of caspase-3 are described. From extended tethering, a salicylic acid fragment was identified as having binding affinity for the S-4 pocket of caspase-3. X-ray crystallography and molecular modeling of the initial tethering hit resulted in the synthesis of 4, which reversibly inhibited caspase-3 with a K-i = 40 nM. Further optimization led to the identification of a series of potent and selective inhibitors with K-i values in the 20-50 nM range. One of the most potent compounds in this series, 66b, inhibited caspase-3 with a K-i = 20 nM and selectivity of 8-500-fold for caspase-3 vs a panel of seven caspases (1, 2, and 4-8). A high-resolution X-ray cocrystal structure of 4 and 66b supports the predicted binding modes of our compounds with caspase-3.

  DOI：

  10.1021/jm020230j

文献信息

• Method for treating glaucoma
  申请人：Pfizer Inc.

  公开号：US06344485B1

  公开（公告）日：2002-02-05

  Methods of using prostaglandin agonists for the reduction of intraocular pressure, and accordingly glaucoma.

  使用前列腺素激动剂降低眼内压及相应青光眼的方法。
• Prostaglandin agonists and their use to treat bone disorders
  申请人：Pfizer Inc.

  公开号：US06498172B1

  公开（公告）日：2002-12-24

  This invention relates to prostaglandin agonists, methods of using such prostaglandin agonists, pharmaceutical compositions containing such prostaglandin agonists and kits containing such prostaglandin agonists. The prostaglandin agonists are useful for the treatment of bone disorders including osteoporosis.

  本发明涉及前列腺素受体激动剂、使用此类前列腺素受体激动剂的方法、含有此类前列腺素受体激动剂的药物组合物以及含有此类前列腺素受体激动剂的试剂盒。这些前列腺素受体激动剂可用于治疗包括骨质疏松症在内的骨骼疾病。
• Methods of treatment using an EP2 selective receptor agonist
  申请人：Constan A. Alexander

  公开号：US20050203086A1

  公开（公告）日：2005-09-15

  The present invention relates to methods of treating pulmonary hypertension, facilitating joint fusion, facilitating tendon and ligament repair, reducing the occurrence of secondary fracture, treating avascular necrosis, facilitating cartilage repair, facilitating bone healing after limb transplantation, facilitating liver regeneration, facilitating wound healing, reducing the occurrence of gastric ulceration, treating hypertension, facilitating the growth of tooth enamel or finger or toe nails, treating glaucoma, treating ocular hypertension, and repairing damage caused by metastatic bone disease using an EP 2 selective receptor agonist.

  本发明涉及使用EP2选择性受体激动剂治疗肺动脉高压、促进关节融合、促进肌腱和韧带修复、减少继发性骨折的发生、治疗缺血性坏死、促进软骨修复、促进肢体移植后的骨愈合、促进肝脏再生、促进伤口愈合、减少胃溃疡的发生、治疗高血压、促进牙齿珐琅质或手指甲和脚趾甲的生长、治疗青光眼、治疗眼高压以及修复由转移性骨疾病引起的损伤的方法。
• Prevention of loss and restoration of bone mass by certain prostaglandin agonists
  申请人：Pfizer Inc.

  公开号：US06288120B1

  公开（公告）日：2001-09-11

  Prostaglandin agonists of formula (I), in which, for example, A is a sulphonyl or acyl group, B is N or CH, M contains a ring and K and Q are linking groups, methods of using such prostaglandin agonists, pharmaceutical compositions containing such prostaglandin agonists and kits useful for the treatment of bone disorders including osteoporosis.

  前列腺素激动剂公式(I)，其中，例如，A是磺酰基或酰基，B是N或CH，M含有一个环，K和Q是连接基团，使用这种前列腺素激动剂的方法，包含这种前列腺素激动剂的药物组合物以及用于治疗包括骨质疏松症在内的骨病的试剂盒。
• [EN] FACTOR XIa INHIBITORS<br/>[FR] INHIBITEURS DE FACTEUR XIA
  申请人：MERCK SHARP & DOHME

  公开号：WO2016168098A1

  公开（公告）日：2016-10-20

  The present invention provides a compound of Formula (I); and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.

  本发明提供了一种公式(I)的化合物；以及包含一个或多个所述化合物的药物组合物，以及使用所述化合物治疗或预防血栓、栓塞、高凝状态或纤维化变化的方法。这些化合物是选择性的因子XIa抑制剂或对因子XIa和血浆激肽酶的双重抑制剂。