苄基[2-(5-羟基吲哚-3-基)-乙基]氨基甲酸酯 | 53157-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基[2-(5-羟基吲哚-3-基)-乙基]氨基甲酸酯
• 中文别名: [2-(5-羟基吲哚-3-基)-乙基]氨基甲酸苄酯
• 英文名称: N-benzyloxycarbonyl-5-hydroxytryptamine
• 英文别名: Benzyl (2-(5-hydroxy-1H-indol-3-yl)ethyl)carbamate；benzyl N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]carbamate
• CAS: 53157-50-9
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: OFYSKCJCRYHZAN-UHFFFAOYSA-N

物化性质

• 沸点：
  590.1±50.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  苄基[2-(5-羟基吲哚-3-基)-乙基]氨基甲酸酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 5-羟基色胺
  参考文献：
  名称：

  Taniguchi, Mikio; Anjiki, Tomiko; Nakagawa, Masako, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 7, p. 2544 - 2554

  摘要：

  DOI：
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 生成 苄基[2-(5-羟基吲哚-3-基)-乙基]氨基甲酸酯
  参考文献：
  名称：

  Hino, Tohru; Taniguchi, Mikio; Nakagawa, Masako, Heterocycles, 1981, vol. 15, # 1, p. 187 - 190

  摘要：

  DOI：

文献信息

• An unusual by-product in a concise synthesis of a rotationally restricted phenolic analog of serotonin
  作者：John E. Macor

  DOI：10.1016/0040-4039(95)01453-o

  日期：1995.9

  An improved synthesis of a dihydropyrano[3,-2e]indole analog (4, CP-123,479) of serotonin has been accomplished. Starting with serotonin itself and utilizing a Claisen rearrangement/cyclization of a 5-propargyloxy-N-Cbz-tryptamine (2) to form the pyrano[3,2-e]indole in 3, the reaction sequence of four steps afforded a 36% overall yield of 4. In the conversion of 2 to 3, a unique tetracyclic by-product

  已完成5-羟色胺的二氢吡喃并[3，-2e]吲哚类似物（4，CP-123,479）的改进合成。从5-羟色胺本身开始，并利用5-炔丙基氧基-N-Cbz-色胺（2）的克莱森重排/环化反应，以3的形式形成吡喃并[3,2-e]吲哚，四步反应得到的收率为36％总产率为4。在2至3的转化中，观察到独特的四环副产物（5），其由Cbz基团的-NH-生成，并横跨所形成的吡喃并[3,2-e]吲哚中的烯烃。从5到叔胺（6）的转化增加了对四环结构鉴定的确认。
• 一种海鞘素类化合物、其抗体药物偶联物及其应用
  申请人：苏州宜联生物医药有限公司

  公开号：CN116284054A

  公开（公告）日：2023-06-23

  本发明公开了一种海鞘素类化合物、其抗体药物偶联物及其应用。本发明提供了一种海鞘素类化合物或其药学上可接受的盐。本发明的抗体药物偶联物，可以实现肿瘤富集，消除或降低海鞘素作用于非疾病组织而引起的毒副作用，提高治疗效果。
• Ester and amide derivatives of E64c as inhibitors of platelet calpains
  作者：Zhenya Huang、Eleanor B. McGowan、Thomas C. Detwiler

  DOI：10.1021/jm00089a015

  日期：1992.5

  Ester and amide derivatives of E64c, (+)-(2S,3S)-3-[[(S)-3-methyl-1-[(3-methylbutyl)carbamoyl]butyl]carbamoyl]-2-oxiranecarboxylic acid, an inhibitor of calpains, were synthesized and tested for ability to inhibit calpain in lysed cells, ability to enter intact cells, and ability to inhibit calpain in intact cells. The esters were from halogen-substituted alcohols and alcohols with increasing size. There were no appreciable differences in the inhibitory potency of any of the halogen-substituted esters from ethyl to trifluoroethyl, indicating that ease of hydrolysis of this class of ester is not important for activity. The only ester with impaired activity was the largest, Z-leucyl-norleucyl, which was about 5% as effective as the ethyl ester, E64d. Amides of amino acid esters also had impaired activity. To explore the possibility of targeting E64c derivatives to specific cells, esters and amides of E64c with 5-hydroxytryptamine were tested on the rationale that the active 5-hydroxytryptamine uptake mechanism of platelets might selectively concentrate the drug in platelets. Both the ester and amide inhibited calpain in lysed cells, but only the ester inhibited in intact cells. The 5-hydroxytryptamine ester showed no advantage over the ethyl ester in entering platelets.
• A Practicable Synthesis of 3-(2-Aminoethyl)-1<i>H</i>-indol-5-yl Hydrogen Sulfate (Serotonin<i>O</i>-Sulfate)
  作者：Janos Borgulya、Karl Bernauer

  DOI：10.1055/s-1983-30205

  日期：——
• EP0754041A4
  申请人：——

  公开号：EP0754041A4

  公开（公告）日：1997-11-19