Ethyl 9-p-chlorobenzyl-6-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetate | 117200-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Ethyl 9-p-chlorobenzyl-6-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetate
• 英文别名: ethyl 2-[9-[(4-chlorophenyl)methyl]-6-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetate
• CAS: 117200-35-8
• 化学式: C₂₄H₂₆ClNO₄S
• 分子量: 459.994
• InChiKey: PSNKQMOQXBDXBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 9-p-chlorobenzyl-6-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 9-p-Chlorobenzyl-6-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetic acid
  参考文献：
  名称：

  Identification of an indole series of prostaglandin D2 receptor antagonists

  摘要：

  A novel indole series of PGD(2) receptor (DP receptor) antagonists is presented. Optimization of this series led to the identification of potent and selective DP receptor antagonists. In particular, antagonists 35 and 36 were identified with K-i values of 2.6 and 1.8 nM, respectively. These two antagonists are also potent in a DIP functional assay where they inhibit the PGD(2) induced cAMP production in platelet rich plasma with IC50 values of 7.9 and 8.6 W, respectively. The structure-activity relationships of this indole series of DP receptor antagonists will also be discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.062
• 作为产物：
  描述：

  ethyl 9-p-chlorobenzyl-6-methylsulfinyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetate 、 间氯过氧苯甲酸 在 碳酸氢钠 、 水 、 Brine 、 crude product 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 18.0h， 以yielded 200 mg (42%) of the pure title compound的产率得到Ethyl 9-p-chlorobenzyl-6-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetate
  参考文献：
  名称：

  Tetrahydrocarbazole esters, pharmaceutical compositions and use

  摘要：

  本发明公开了四氢咔唑酯化合物。这些化合物作为前列腺素和血栓素拮抗剂，在治疗哮喘、腹泻、高血压、心绞痛、血小板聚集、脑血管痉挛、早产、自发流产、痛经和环孢霉素A引起的肾毒性以及细胞保护剂方面具有用途。

  公开号：

  US04940719A1

文献信息

• Tetrahydrocarbazole esters
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0239306A2

  公开（公告）日：1987-09-30

  Tetrahydrocarbazole esters are disclosed. The compounds act as prostaglandin and thromboxane antagonists and are useful in treating asthma, diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion and dysmenorrhea and as cytoprotective agents.

  这些化合物是前列腺素和血栓素拮抗剂，可用于治疗哮喘、腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自然流产和痛经，还可作为细胞保护剂。
• US4940719A
  申请人：——

  公开号：US4940719A

  公开（公告）日：1990-07-10
• Identification of an indole series of prostaglandin D2 receptor antagonists
  作者：Claudio F. Sturino、Nicolas Lachance、Michael Boyd、Carl Berthelette、Marc Labelle、Lianhai Li、Bruno Roy、John Scheigetz、Nancy Tsou、Christine Brideau、Elizabeth Cauchon、Marie-Claude Carriere、Danielle Denis、Gillian Greig、Stacia Kargman、Sonia Lamontagne、Marie-Claude Mathieu、Nicole Sawyer、Deborah Slipetz、Gary O’Neill、Zhaoyin Wang、Robert Zamboni、Kathleen M. Metters、Robert N. Young

  DOI：10.1016/j.bmcl.2006.02.062

  日期：2006.6

  A novel indole series of PGD(2) receptor (DP receptor) antagonists is presented. Optimization of this series led to the identification of potent and selective DP receptor antagonists. In particular, antagonists 35 and 36 were identified with K-i values of 2.6 and 1.8 nM, respectively. These two antagonists are also potent in a DIP functional assay where they inhibit the PGD(2) induced cAMP production in platelet rich plasma with IC50 values of 7.9 and 8.6 W, respectively. The structure-activity relationships of this indole series of DP receptor antagonists will also be discussed. (c) 2006 Elsevier Ltd. All rights reserved.
• Tetrahydrocarbazole esters, pharmaceutical compositions and use
  申请人：Merck Frosst Canada, Inc.

  公开号：US04940719A1

  公开（公告）日：1990-07-10

  Tetrahydrocarbazole esters are disclosed. The compounds act as prostaglandin and thromboxane antagonists and are useful in treating asthma, diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion and dysmenorrhea and nephrotoxicity caused by cyclosporin A and as cytoprotective agents.

  四氢咔唑酯已被披露。这些化合物作为前列腺素和血栓素拮抗剂，并且在治疗哮喘、腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自发流产、痛经和环孢霉素A引起的肾毒性以及作为细胞保护剂方面具有用处。