N¹-benzyl-(L)-tryptophan methyl ester | 129784-64-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N¹-benzyl-(L)-tryptophan methyl ester
• 英文别名: (S)-(-)-N'-benzyltryptophan methyl ester；(S)-(-)-1-benzyl-tryptophan methyl ester；methyl (2S)-2-amino-3-(1-benzylindol-3-yl)propanoate
• CAS: 129784-64-1
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: HGLYUTGPOMYFQT-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹-benzyl-(L)-tryptophan methyl ester 在 sodium tetrahydroborate 、 三甲基氯硅烷 作用下， 以 1,4-二氧六环 、 甲醇 、 苯 为溶剂， 反应 37.0h， 生成 (1S,3S)-(-)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate
  参考文献：
  名称：

  Studies on Gelsemium alkaloids. Total synthesis of (+)-koumine, (+)-taberpsychine, and (+)-koumidine

  摘要：

  DOI：

  10.1021/ja00169a033
• 作为产物：
  描述：

  N-[叔丁氧羰基]-L-色氨酸甲酯 在 potassium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N¹-benzyl-(L)-tryptophan methyl ester
  参考文献：
  名称：

  分子内逆电子需量Diels-色胺与束缚的杂芳族氮杂二氮烯的Alder反应1

  摘要：

  通过乙胺侧链束缚在色胺上的1,2,4,5-四嗪和1,2,4-三嗪经历分子内逆电子需量环加成反应，生成了具有白色胚芽孢生物碱的[ABazaCE]环骨架的加合物。

  DOI：

  10.1016/s0040-4020(00)00003-x

文献信息

• MITHRAMYCIN DERIVATIVES HAVING INCREASED SELECTIVITY AND ANTI-CANCER ACTIVITY
  申请人：University of Kentucky Research Foundation

  公开号：US20190083519A1

  公开（公告）日：2019-03-21

  Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.

  米司麦霉素侧链羧酸（MTM-SA）衍生物包括一种取代氨基酸衍生物、一种取代氨基酸二肽衍生物或一种未取代的二肽衍生物。这些MTM-SA衍生物对于治疗与异常红细胞转化特异性转录因子相关的癌症或神经疾病很有用。独特的MTM-SA衍生物对ETS转录因子具有增强的选择性。
• Inverse electron demand Diels-Alder reactions of indole V. Reactions of 3-substituted indoles with heteroaromatic azadienes
  作者：Scott C. Benson、Lily Lee、John K. Snyder

  DOI：10.1016/0040-4039(96)01017-9

  日期：1996.7

  The inverse electron demand Diels-Alder reactions of 3-substituted indoles with 1,2,4-triazines and 1,2,4,5-tetrazines proceeded in excellent yields both inter- and intramolecularly. The cycloaddition of tryptophan with a tethered 1,2,4-triazine produced a diastereomerically pure cycloadduct.

  3-取代的吲哚与1,2,4-三嗪和1,2,4,5-四嗪的电子反需求Diels-Alder反应在分子间和分子内均以优异的产率进行。色氨酸与束缚的1,2,4-三嗪的环加成反应生成非对映体纯的环加合物。
• Alpha-amino-indole-3-acetic acids useful as anti-diabetic, anti-obesity and anti-atherosclerotic agents
  申请人：THE UPJOHN COMPANY

  公开号：EP0375133A1

  公开（公告）日：1990-06-27

  Provided are novel α-aminoindole-3-acetic acid derivatives having the formula wherein R through R9 are the same as in Claim 1; and pharmacologically acceptable salts of compounds wherein R₉ is not OM, which are useful as anti-diabetic, anti-obesity and anti-athero­sclerotic agents.

  本发明提供了新型α-氨基吲哚-3-乙酸衍生物，其式为 其中 R 至 R9 与权利要求 1 中的相同；以及其中 R𠢙 不为 OM 的化合物的药理学上可接受的盐，可用作抗糖尿病、抗肥胖和抗动脉粥样硬化药物。
• Mithramycin derivatives having increased selectivity and anti-cancer activity
  申请人：University of Kentucky Research Foundation

  公开号：US11224609B2

  公开（公告）日：2022-01-18

  Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.

  提供了米曲霉素侧链羧酸（MTM-SA）衍生物，其中包括取代的氨基酸衍生物、取代的氨基酸二肽衍生物或未取代的二肽衍生物。MTM-SA 衍生物可用于治疗与红细胞转化特异性转录因子异常有关的癌症或神经疾病。独特的 MTM-SA 衍生物对 ETS 转录因子的选择性增加。
• Development of Mithramycin Analogues with Increased Selectivity toward ETS Transcription Factor Expressing Cancers
  作者：Prithiba Mitra、Joseph M. Eckenrode、Abhisek Mandal、Amit K. Jha、Shaimaa M. Salem、Markos Leggas、Jürgen Rohr

  DOI：10.1021/acs.jmedchem.8b01107

  日期：2018.9.13

  Mithramycin A (1) was identified as the top potential inhibitor of the aberrant ETS transcription factor EWSFLI1, which causes Ewing sarcoma. Unfortunately, 1 has a narrow therapeutic window, compelling us to seek less toxic and more selective analogues. Here, we used MTMSA (2) to generate analogues via peptide coupling and fragment-based drug development strategies. Cytotoxicity assays in ETS and non-ETS dependent cell lines identified two dipeptide analogues, 60 and 61, with 19.1- and 15.6-fold selectivity, respectively, compared to 1.5-fold for 1. Importantly, the cytotoxicity of 60 and 61 is <100 nM in ETS cells. Molecular assays demonstrated the inhibitory capacity of these analogues against EWS-FLI1 mediated transcription in Ewing sarcoma. Structural analysis shows that positioning the tryptophan residue in a distal position improves selectivity, presumably via interaction with the ETS transcription factor. Thus, these analogues may present new ways to target transcription factors for clinical use.