methyl (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoate | 89434-07-1

• 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: methyl (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoate
• CAS: 89434-07-1
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: ZLVRWEGIPKKGJL-NSHDSACASA-N

物化性质

• 熔点：
  92-95 °C
• 沸点：
  425.6±40.0 °C(Predicted)
• 密度：
  1.246±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：
  77.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoate 在 lithium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-2-(2-Bromo-benzoylamino)-3-(5-methoxy-1H-indol-3-yl)-propionic acid
  参考文献：
  名称：

  N-Benzoyl amino acids as LFA-1/ICAM inhibitors 1: amino acid structure–activity relationship

  摘要：

  The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00084-2
• 作为产物：
  描述：

  2-碘-4-甲氧基苯基胺 在 三乙烯二胺 、 盐酸 、 palladium diacetate 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Development of Mithramycin Analogues with Increased Selectivity toward ETS Transcription Factor Expressing Cancers

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.8b01107

文献信息

• Direct C4-Acetoxylation of Tryptophan and Tryptophan-Containing Peptides <i>via</i> Palladium(II)-Catalyzed C–H Activation
  作者：Qiyu Zhang、Xiong Xie、Jingjing Peng、Feiyang Chen、Jinyu Ma、Chunpu Li、Hong Liu、Dechuan Wang、Jiang Wang

  DOI：10.1021/acs.orglett.1c01434

  日期：2021.6.18

  An efficient regioselective palladium(II)-catalyzed C(sp2)–H 4-acetoxylation of tryptophan and tryptophan-containing peptides is described. This transformation achieves the direct construction of C–O bonds at the tryptophan C4-position and features good functional group tolerance. The 4-hydroxyl compound was obtained by removing acetyl after C4-acetoxylation of tryptophan derivatives and tryptophan-containing

  描述了色氨酸和含色氨酸肽的高效区域选择性钯 （II） 催化的 C（sp2）-H 4-乙酰氧基化。这种转变实现了在色氨酸 C4 位的直接构建 C-O 键，并具有良好的官能团耐受性。色氨酸衍生物和含色氨酸的二肽经 C4-乙酰化后去除乙酰基而得 4-羟基化合物。该方法为合成 4-取代色氨酸衍生物和修饰含色氨酸的肽提供了一种新的策略。
• 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。
• Chemical compounds
  申请人：——

  公开号：US20030225092A1

  公开（公告）日：2003-12-04

  Compounds of the general structural formula (I) and use of the compounds and salts and solvates thereof, as therapeutic agents. 1

  通用结构式（I）的化合物及其盐和溶剂合物的使用，作为治疗剂。
• [EN] 5-METHOXYTRYPTOPHAN AND ITS DERIVATIVES AND USES THEREOF<br/>[FR] 5-MÉTHOXYTRYPTOPHANE ET SES DÉRIVÉS, ET LEURS UTILISATIONS
  申请人：NAT HEALTH RESEARCH INSTITUTES

  公开号：WO2016115188A1

  公开（公告）日：2016-07-21

  A 5-methoxytryptophan and its derivatives are disclosed, wherein the 5-methoxytryptophan and its derivatives are represented by the following formula (I): (I) wherein R1, R2, R3, R4, R5, and n are defined in the specification. In addition, the present invention also provides novel used of the 5-methoxytryptophan and its derivatives for treating inflammatory-related disease and cancers.

  本发明公开了5-甲氧基色氨酸及其衍生物，其中5-甲氧基色氨酸及其衍生物由以下式子（I）表示：（I）其中R1、R2、R3、R4、R5和n在说明书中定义。此外，本发明还提供了5-甲氧基色氨酸及其衍生物用于治疗与炎症相关的疾病和癌症的新用途。
• Facile and Efficient One-Pot Synthesis of β-Carbolines
  作者：Jian-Guo Tang、Han Liu、Zhong-Yu Zhou、Ji-Kai Liu

  DOI：10.1080/00397910903097245

  日期：2010.4.26

  tetrahydrocarboline 3 from tryptophan methyl ester 1 and aldehyde 2 by Pictet–Spengler reaction, followed by treatment with trichlorocyanuric acid, provides a facile and efficient route for a one-pot synthesis of β-carbolines with excellent yields.

  通过 Pictet-Spengler 反应从色氨酸甲酯 1 和醛 2 初步形成四氢咔啉 3，然后用三氯氰尿酸处理，为以优异的收率一锅法合成 β-咔啉提供了一种简便有效的途径。