N-ethyl-L-tryptophanamide | 53708-64-8

• 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: N-ethyl-L-tryptophanamide
• 英文别名: tryptophan ethyl amide；L-tryptophan-ethylamide；L-Tryptophan-aethylamid；(2S)-2-amino-N-ethyl-3-(1H-indol-3-yl)propanamide
• CAS: 53708-64-8
• 化学式: C₁₃H₁₇N₃O
• mdl: MFCD13244747
• 分子量: 231.297
• InChiKey: ITMWMUMGRHXBTK-NSHDSACASA-N

物化性质

• 沸点：
  515.4±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  70.9
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-ethyl-L-tryptophanamide 在 sodium tetrahydroborate 、 TEA 、 sodium cyanoborohydride 、 sodium carbonate 、 三氟乙酸 、 原甲酸三甲酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.83h， 生成 (1S,2R,10S,12S)-13-benzyl-15-ethyl-1-methyl-3,13,15-triazatetracyclo[10.2.2.02,10.04,9]hexadeca-4,6,8-triene-14,16-dione
  参考文献：
  名称：

  Stereoselective Transformation of Indole Diazabicyclo[3.2.2]nonedione to Azepinoindole

  摘要：

  [GRAPHICS]The synthesis of an indole diazabicyclo[3.2.2]nonedione derivative was achieved in a few steps starting from L-tryptophan. Reduction with borane-THF complex leads to fragmentation of the bicycle and the stereoselective formation of an azepinoindole derivative was observed.

  DOI：

  10.1021/ol0271990
• 作为产物：
  描述：

  N-叔丁氧羰基-L-色氨酸 在 盐酸 、 TEA 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.0h， 生成 N-ethyl-L-tryptophanamide
  参考文献：
  名称：

  Stereoselective Transformation of Indole Diazabicyclo[3.2.2]nonedione to Azepinoindole

  摘要：

  [GRAPHICS]The synthesis of an indole diazabicyclo[3.2.2]nonedione derivative was achieved in a few steps starting from L-tryptophan. Reduction with borane-THF complex leads to fragmentation of the bicycle and the stereoselective formation of an azepinoindole derivative was observed.

  DOI：

  10.1021/ol0271990

文献信息

• Tryptophan Lyase (NosL): A Cornucopia of 5′-Deoxyadenosyl Radical Mediated Transformations
  作者：Dhananjay M. Bhandari、Dmytro Fedoseyenko、Tadhg P. Begley

  DOI：10.1021/jacs.6b06139

  日期：2016.12.21

  Tryptophan lyase (NosL) is a radical S-adenosyl-l-methionine (SAM) enzyme that catalyzes the formation of 3-methyl-2-indolic acid from l-tryptophan. In this paper, we demonstrate that the 5'-deoxyadenosyl radical is considerably more versatile in its chemistry than previously anticipated: hydrogen atom abstraction from Nα-cyclopropyltryptophan occurs at Cα rather than the amino group with NosL Y90A

  色氨酸裂解酶 (NosL) 是一种自由基 S-腺苷-l-甲硫氨酸 (SAM) 酶，可催化从 l-色氨酸形成 3-甲基-2-吲哚酸。在本文中，我们证明了 5'-脱氧腺苷基团在其化学中的用途比以前预期的要多得多：从 Nα-环丙基色氨酸中提取氢原子发生在 Cα 处，而不是使用 NosL Y90A 的氨基，并用酮代替底物胺或烯烃将化学反应从氢原子提取变为双键加成。此外，5'-脱氧腺苷自由基可以添加到 [4Fe-4S] 簇中，并且连二亚硫酸盐可用于在活性位点捕获自由基。
• Novel Lipopeptides as Antibacterial Agents
  申请人：Hill Jason

  公开号：US20090011977A1

  公开（公告）日：2009-01-08

  The present invention relates to novel lipopeptide compounds. The invention also relates to pharmaceutical compositions of these compounds and methods of using these compounds as antibacterial compounds. The invention also relates to methods of producing these novel lipopeptide compounds and intermediates used in producing these compounds.

  本发明涉及新型脂肽化合物。本发明还涉及这些化合物的药物组合物以及将这些化合物用作抗菌化合物的方法。本发明还涉及生产这些新型脂肽化合物的方法以及用于生产这些化合物的中间体。
• 基于马钱苷的类单萜吲哚生物碱及其合成方法和应用、防治糖尿病或糖尿病肾病的药物
  申请人：大理大学

  公开号：CN115650981A

  公开（公告）日：2023-01-31

  本发明提供了基于马钱苷的类单萜吲哚生物碱及其合成方法和应用、防治糖尿病或糖尿病肾病的药物，属于药物化学技术领域。本发明提供的类单萜吲哚生物碱源于天然产物马钱苷，相较于极性很大的马钱苷，其极性低，脂溶性好，有利于其在体内的吸收。本发明提供的类单萜吲哚生物碱具有高效抗糖尿病和糖尿病肾病活性，可以用于制备防治糖尿病或糖尿病肾病的药物。本发明提供了所述类单萜吲哚生物碱的合成方法，本发明提供的方法操作简单，适宜规模化生产。
• Synthesis, in Vitro Anti-Breast Cancer Activity, and Intracellular Decomposition of Amino Acid Methyl Ester and Alkyl Amide Phosphoramidate Monoesters of 3‘-Azido-3‘-deoxythymidine (AZT)
  作者：Vidhya V. Iyer、George W. Griesgraber、Matthew R. Radmer、Edward J. McIntee、Carston R. Wagner

  DOI：10.1021/jm000110g

  日期：2000.6.1

  We report the synthesis and anticancer activity of a series of AZT phosphoramidate monoesters containing amino acid methyl ester (3a-11a) and N-alkyl amide (3b-11b, 9c-9f) moieties. The aromatic amino acid methyl esters were found to be more cytotoxic than the aliphatic analogues toward MCF-7 cells (human pleural effusion breast adenocarcinoma cell line). A marked stereochemical preference for the L-amino acid stereochemistry was also observed in MCF-7 cells. There was no consistent enhancement of cytotoxicity of the methyl amides over the corresponding methyl esters. AZT and the two AZT aromatic amino acid methyl ester phosphoramidates 8a and 9a were found to be more cytotoxic toward MCF-7 cells than to CEM cells (human T-cell lymphoblastic leukemia). The selective cytotoxicity toward MCF-7 cells may be associated with greater intracellular levels of phosphoramidate monoester and/or phosphorylated AZT.
• Bauguess; Berg, Journal of Biological Chemistry, 1934, vol. 106, p. 615,616
  作者：Bauguess、Berg

  DOI：——

  日期：——