(1,2,3,4-tetrahydro-carbazol-1-yl)-acetic acid ethyl ester | 58928-88-4

• 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: (1,2,3,4-tetrahydro-carbazol-1-yl)-acetic acid ethyl ester
• 英文别名: ethyl 2-(2,3,4,9-tetrahydro-1H-carbazol-1-yl)acetate
• CAS: 58928-88-4
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: WNDCOGOHXMFTDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1,2,3,4-tetrahydro-carbazol-1-yl)-acetic acid ethyl ester 在 吡啶 、 lithium aluminium tetrahydride 、 氢化钾 、 叔丁醇 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 1,2,2a,3,4,5-hexahydropyrrolo<3,2,1-jk>carbazole
  参考文献：
  名称：

  2,3-二氢-1 H-吡咯并[1,2- a ]吲哚，2,3-二氢-9-甲基-1 H-吡咯并[1,2- a ]吲哚，1,2,2a的制备，3,4,5-六氢吡咯并[3,2,1- jk ]咔唑和2,3,3a，4,5,6-六氢-1 H-吡啶并[3,2,1- jk ]咔唑

  摘要：

  已经研究了制备标题中列出的四种化合物的几种途径，以决定适合于大量获取材料的方法。

  DOI：

  10.1039/p19800000097
• 作为产物：
  描述：

  (1,2,3,4-四氢-咔唑-1-基)-乙酸 生成 (1,2,3,4-tetrahydro-carbazol-1-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  ASSELIN A. A.; HUMBER L. G.; DOBSON T. A.; KOMLOSSY J.; MARTEL R. R., J. MED. CHEM. , 1976, 19, NO 6, 787-792

  摘要：

  DOI：

文献信息

• 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。
• 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.
• BAILEY A. S.; SCOTT P. W.; VANDREVALA M. H., J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 1, 97-101
  作者：BAILEY A. S.、 SCOTT P. W.、 VANDREVALA M. H.

  DOI：——

  日期：——
• METHODS AND COMPOSITIONS FOR INHIBITING OR REDUCING HAIR LOSS, ACNE, ROSACEA, PROSTATE CANCER, AND BPH
  申请人：Cotsarelis George

  公开号：US20110021599A1

  公开（公告）日：2011-01-27

  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.
• US9254293B2
  申请人：——

  公开号：US9254293B2

  公开（公告）日：2016-02-09