5-HTP乙酯 | 43157-32-0

• 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
• 中文名称: 5-HTP乙酯
• 英文名称: 5-hydroxytryptophan esthyl ester
• 英文别名: 5-hydroxytryptophan ethyl ester；5-HTP ethyl ester；5-Hydroxy-tryptophan-aethylester；5-Hydroxy-DL-tryptophan ethyl ester；ethyl 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate
• CAS: 43157-32-0
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: HIHZWVKQSWRKCO-UHFFFAOYSA-N

物化性质

• 沸点：
  460.1±40.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  88.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-HTP乙酯 、 N-(2-甲酰基-5,8-二氧代-5,8-二氢喹啉-7-基)乙酰胺 以 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 以48%的产率得到7-N-acetyl-11'-hydroxydemethyllavendamycin ethyl ester
  参考文献：
  名称：

  Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents

  摘要：

  A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were prepared through Pictet-Spengler condensation of the desired 2-formylquinoline-5,8-diones with the required tryptophans followed by further needed transformations. Metabolism and toxicity studies demonstrated that the best substrates for NQO1 were also the most selectively toxic to NQO1-rich tumor cells compared to NQO1-deficient tumor cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.037
• 作为产物：
  描述：

  5-羟基色氨酸 在 盐酸 作用下， 生成 5-HTP乙酯
  参考文献：
  名称：

  Synthesis in the 5-Hydroxyindole Series. N-Acetyl-5-hydroxytryptophan and Related Compounds

  摘要：

  DOI：

  10.1021/jo01084a008

文献信息

• [EN] NOVEL HDAC6 INHIBITORS AND THEIR USES<br/>[FR] NOUVEAUX INHIBITEURS DE HDAC6 ET LEURS UTILISATIONS
  申请人：UNIVERSITÄT REGENSBURG

  公开号：WO2016020369A1

  公开（公告）日：2016-02-11

  The present invention relates to small molecule compounds and their use as HDAC inhibitors and in the treatment of various diseases, such as cancer. The present invention further relates to methods of synthesizing the compounds and methods of treatment. H − L(HA), H is a head group selected from (head group 1), (head group 2), (head group 3), (head group 4), (head group 5) and (head group 6).

  本发明涉及小分子化合物及其作为HDAC抑制剂的用途以及在治疗各种疾病（如癌症）中的应用。本发明还涉及合成这些化合物的方法和治疗方法。H - L（HA），其中H是从（头基团1）、（头基团2）、（头基团3）、（头基团4）、（头基团5）和（头基团6）中选择的头基团。
• NOVEL HDAC6 INHIBITORS AND THEIR USES
  申请人：Universität Regensburg

  公开号：US20170210743A1

  公开（公告）日：2017-07-27

  The present invention relates to small molecule compounds and their use as HDAC inhibitors and in the treatment of various diseases, such as cancer. The present invention further relates to methods of synthesizing the compounds and methods of treatment. H-L(HA), H is a head group selected from (head group 1), (head group 2), (head group 3), (head group 4), (head group 5) and (head group 6).
• US4908322A
  申请人：——

  公开号：US4908322A

  公开（公告）日：1990-03-13
• Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents
  作者：Wen Cai、Mary Hassani、Rajesh Karki、Ervin D. Walter、Katherine H. Koelsch、Hassan Seradj、Jayana P. Lineswala、Hamid Mirzaei、Jeremy S. York、Fatemeh Olang、Minoo Sedighi、Jennifer S. Lucas、Thomas J. Eads、Anthony S. Rose、Sahba Charkhzarrin、Nicholas G. Hermann、Howard D. Beall、Mohammad Behforouz

  DOI：10.1016/j.bmc.2010.01.037

  日期：2010.3

  A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were prepared through Pictet-Spengler condensation of the desired 2-formylquinoline-5,8-diones with the required tryptophans followed by further needed transformations. Metabolism and toxicity studies demonstrated that the best substrates for NQO1 were also the most selectively toxic to NQO1-rich tumor cells compared to NQO1-deficient tumor cells. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis in the 5-Hydroxyindole Series. N-Acetyl-5-hydroxytryptophan and Related Compounds
  作者：JOHN KOO、SOUREN AVAKIAN、GUSTAV J. MARTIN

  DOI：10.1021/jo01084a008

  日期：1959.2