6-methylbenzothiophene-3-carboxylic acid | 82787-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-methylbenzothiophene-3-carboxylic acid
• 英文别名: 6-methylbenzo[b]thiophene-3-carboxylic acid；6-Methyl-1-benzothiophene-3-carboxylic acid
• CAS: 82787-84-6
• 化学式: C₁₀H₈O₂S
• mdl: MFCD03419862
• 分子量: 192.238
• InChiKey: LGPZMCSOENSZPL-UHFFFAOYSA-N

物化性质

• 熔点：
  205-209 °C
• 沸点：
  386.1±22.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methylbenzothiophene-3-carboxylic acid 在 盐酸 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 甲醇 、 四氯化碳 、 水 为溶剂， 反应 11.0h， 生成 6-(1H-imidazol-1-ylmethyl)benzo[b]thiophene-3-carboxylic acid
  参考文献：
  名称：

  Selective thromboxane synthetase inhibitors. 3. 1H-Imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene- and indole-2- and 3-carboxylic acids

  摘要：

  The preparation of a series of 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indolecarboxylic acids is described. Most of the compounds were potent inhibitors of TxA2 synthetase in vitro, and the distance between the imidazole and carboxylic acid groups was found to be important for optimal potency. The most potent compound in vivo was 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), which, in conscious dogs, showed a similar profile of activity to that of dazoxiben (1).

  DOI：

  10.1021/jm00159a012
• 作为产物：
  描述：

  3-bromo-6-methylbenzothiophene 在 正丁基锂 、 二氧化碳 作用下， 以 正己烷 、 水 为溶剂， 生成 6-methylbenzothiophene-3-carboxylic acid
  参考文献：
  名称：

  Heterocyclic thromboxane synthetase inhibitors and pharmaceutical

  摘要：

  杂环血栓素合成酶抑制剂的化学式为##STR1##其中R.sup.1，连接到2-、3-或4-位置，是氢、卤素、C.sub.1 -C.sub.4烷基、羟基或C.sub.1 -C.sub.4烷氧基；Y，连接到2-或3-位置，是--COOH、--COO(C.sub.1 -C.sub.4烷基)或--CONH.sub.2；X为O、S、NH、N(C.sub.1 -C.sub.4烷基)或N(苄基)；R，连接到5-、6-或7-位置，是化学式##STR2##或(3-或4-吡啶基)-Z.sup.2-其中Z.sup.1为--CH.sub.2 --、--CH.sub.2 CH.sub.2 --或--CH.sub.2 CH.sub.2 O--，Z.sup.2为--CH.sub.2 --、--CH.sub.2 CH.sub.2 --、--CH.dbd.CH--、--CH.sub.2 O--或--OCH.sub.2 --；以及它们的药学上可接受的盐；它们的制备方法和含有它们的药物组合物。

  公开号：

  US04410539A1

文献信息

• Methods for the treatment of itching comprising administering PGD2 receptor antagonists
  申请人：Shionogi & Co., Ltd.

  公开号：US20030027854A1

  公开（公告）日：2003-02-06

  A PGD 2 receptor antagonist such as a compound of the formula (IA-a-5): 1 a pharmaceutical acceptable salt thereof or a hydrate thereof, has an efficacious activity for the prevention or treatment of itching and is useful as a medicament.

  一种PGD2受体拮抗剂，例如公式（IA-a-5）的化合物：1a其医药上可接受的盐或其水合物，具有预防或治疗瘙痒的有效活性，并可用作药物。
• Heterocyclic thromboxane synthetase inhibitors, processes for their preparation, and pharmaceutical compositions containing them
  申请人：Pfizer Limited

  公开号：EP0050957A1

  公开（公告）日：1982-05-05

  Heterocyclic thromboxane synthetase inhibitors of the formula:- wherein R', which is attached to the 2-, 3- or 4- position, is hydrogen, halogen, C1-C4 alkyl, hydroxy or C1-C4 alkoxy; Y, which is attached to the 2- or 3-position, is -COOH, -COO(C1-C4 alkyl) or-CONH2; X is O, S, NH. N(C1-C4 alkyl) or N(benzyi): and R. which is attached to the 5-, 6- or 7-position, is a group of the formula:- or/3-or 4- pyridyl)-Z2- whereinZ' is.CH2.,-CH2CH2-or-CH2CH2O. and Z2 is-CH2.,-CH2CH2-.-CH=CH--CH2O-or-OCH2-: and their pharmaceutically acceptable satts; processes for their preparation, and pharmaceutical compositions containing them.

  式中的杂环血栓素合成酶抑制剂 其中连接到 2-、3-或 4-位的 R'为氢、卤素、C1-C4 烷基、羟基或 C1-C4 烷氧基； 连接到 2-或 3-位的 Y 是-COOH、-COO（C1-C4 烷基）或-CONH2； X 是 O、S、NHN（C1-C4 烷基）或 N（苄基）： 而连接在 5-、6- 或 7-位的 R.是式中的一个基团：- R. 或/3-或 4-吡啶基）-Z2- 其中Z'是.CH2.,-CH2CH2-或-CH2CH2O.和Z2是-CH2.,-CH2CH2-.-CH=CH--CH2O-或-OCH2-：及其药学上可接受的饱和物；它们的制备工艺和含有它们的药物组合物。
• REMEDIES FOR ITCHING CONTAINING PGD 2? ANTAGONISTS
  申请人：SHIONOGI & CO., LTD.

  公开号：EP1084711A1

  公开（公告）日：2001-03-21

  A PGD2 receptor antagonist such as a compound of the formula (IA-a-5): a pharmaceutical acceptable salt thereof or a hydrate thereof, has an efficacious activity for the prevention or treatment of itching and is useful as a medicament.

  PGD2 受体拮抗剂，如式（IA-a-5）化合物： 其药物可接受盐或其水合物，具有预防或治疗瘙痒的有效活性，可用作药物。
• DRUGS FOR IMPROVING THE PROGNOSIS OF BRAIN INJURY AND A METHOD OF SCREENING THE SAME
  申请人：Japan Science and Technology Agency

  公开号：EP1535629A1

  公开（公告）日：2005-06-01

  There are provided a compound for treatment or prevention of brain injury caused by diseases such as cerebrovascular disorder, brain degenerative disease and demyelinating disease and a method for screening the same. Brain injury in which prostaglandin D2 is participated is treated or prevented by inhibition of hematopoietic prostaglandin D synthase induced in microglia cell or macrophage of brain injury area by diseases such as cerebrovascular disorder, brain degenerative disease or demyelinating disease or by inhibition of activation of prostaglandin D receptor expressed in astroglia cell around the injured area. There is also provided a method of testing those pharmaceutical substances using a transgenic mouse in which human hematopoietic prostaglandin D synthase is expressed in large amounts.

  提供了一种用于治疗或预防脑血管疾病、脑变性疾病和脱髓鞘疾病等疾病引起的脑损伤的化合物及其筛选方法。 通过抑制脑血管疾病、脑变性疾病或脱髓鞘疾病等疾病在脑损伤区域的小胶质细胞或巨噬细胞中诱导的造血前列腺素 D 合成酶，或通过抑制损伤区域周围星形胶质细胞中表达的前列腺素 D 受体的活化，治疗或预防前列腺素 D2 参与的脑损伤。此外，还提供了一种利用大量表达人造血前列腺素 D 合酶的转基因小鼠检测这些药物的方法。
• Drugs for improving prognosis of brain injury
  申请人：Japan Science and Technology Agency

  公开号：EP1598065A2

  公开（公告）日：2005-11-23

  A compound for treatment or prevention of brain injury caused by diseases such as cerebrovascular disorder, brain degenerative disease and demyelinating disease. The compound comprises an antagonist for the prostaglandin D receptor as an effective ingredient. Brain injury in which prostaglandin D2 is a factor is treated or prevented by inhibition of hematopoietic prostaglandin D synthase induced in microglia cell or macrophage of brain area by diseases such as cerebrovascular disorder, brain degenerative disease or demyelinating disease or by inhibition of activation of prostaglandin D receptor expressed in astroglia cell around the injured area.

  一种化合物，用于治疗或预防由脑血管疾病、脑变性疾病和脱髓鞘疾病等疾病引起的脑损伤。该化合物的有效成分包括前列腺素 D 受体拮抗剂。 通过抑制脑血管疾病、脑变性疾病或脱髓鞘疾病等疾病在脑区小胶质细胞或巨噬细胞中诱导的造血前列腺素 D 合成酶，或通过抑制损伤区周围星形胶质细胞中表达的前列腺素 D 受体的活化，治疗或预防以前列腺素 D2 为因素的脑损伤。