Ethyl 9-p-chlorobenzyl-1,2,3,4-tetrahydrocarbazol-1-yl-acetate | 117200-23-4

• 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-1,2,3,4-tetrahydrocarbazol-1-yl-acetate
• 英文别名: ethyl 2-[9-(4-chlorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate；ethyl 2-[9-[(4-chlorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetate
• CAS: 117200-23-4
• 化学式: C₂₃H₂₄ClNO₂
• 分子量: 381.902
• InChiKey: VVJAJHCETCOWQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl 9-p-chlorobenzyl-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-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：

  1-[(4-氯苯基)甲基]-1-(苯基)肼盐酸盐 、 2-环己酮乙酸乙酯 生成 Ethyl 9-p-chlorobenzyl-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

• Prostaglandin D2 receptor antagonists
  申请人：——

  公开号：US20010047027A1

  公开（公告）日：2001-11-29

  Certain tetrahydrocarbazole-1-acetic acid derivatives are potent and selective antagonists of the prostaglandin D2 receptor, and are therefore useful in the treatment of allergic conditions such as allergic rhinitis.

  某些四氢吲哚-1-乙酸衍生物是前列腺素D2受体的强效和选择性拮抗剂，因此在治疗过敏性疾病如过敏性鼻炎方面非常有用。
• Method and compositions for the treatment of allergic conditions using PGD2 receptor antagonists
  申请人：——

  公开号：US20010051624A1

  公开（公告）日：2001-12-13

  Prostaglandin D2 receptor antagonists in conjunction with an antihistamine and/or a leukotriene antagonist are useful in the treatment of allergic conditions.

  前列腺素D2受体拮抗剂结合抗组胺剂和/或白三烯拮抗剂在治疗过敏症状方面是有效的。
• 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。
• Methods and compositions for inhibiting or reducing hair loss, acne, rosacea, prostate cancer, and BPH
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：US10849841B2

  公开（公告）日：2020-12-01

  This invention provides methods of treating androgenetic alopecia (AGA), acne, rosacea, prostate cancer, and benign prostatic hypertrophy (BPH), comprising the step of contacting a subject with a compound or composition capable of decreasing prostaglandin D2 (PGD2) level or activity, a downstream signaling or receptor pathway thereof, or prostaglandin D2 synthase level or activity; methods of stimulating hair growth, comprising the step of contacting a subject with a compound or composition capable of increasing or decreasing the activity or level of a target gene of the present invention, or with a protein product of the target gene or an analogue or mimetic thereof; and methods of testing for AGA and evaluating therapeutic methods thereof, comprising measuring PGD2 levels.

  本发明提供了治疗雄激素性脱发(AGA)、痤疮、酒渣鼻、前列腺癌和良性前列腺肥大(BPH)的方法，包括使受试者与能降低前列腺素D2(PGD2)水平或活性、其下游信号传导或受体通路或前列腺素D2合成酶水平或活性的化合物或组合物接触的步骤；刺激毛发生长的方法，包括使受试者接触能提高或降低本发明靶基因活性或水平的化合物或组合物，或接触靶基因的蛋白产物或其类似物或模拟物；以及检测 AGA 和评估其治疗方法的方法，包括测量 PGD2 水平。
• Method and compositions for the treatment of allergic conditions using pgd2 receptor antagonists
  申请人：——

  公开号：US20030055077A1

  公开（公告）日：2003-03-20

  Prostaglandin D2 receptor antagonists in conjunction with an antihistamine and/or a leukotriene antagonist are useful in the treatment of allergic conditions.

  前列腺素 D2 受体拮抗剂与抗组胺剂和/或白三烯拮抗剂合用，可用于治疗过敏性疾病。