β-methyltryptophan methyl ester, 2RS,3SR isomer | 90243-49-5

• 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: β-methyltryptophan methyl ester, 2RS,3SR isomer
• 英文别名: methyl (2RS,3SR)-2-amino-3-(1H-indol-3-yl)butanoate；(2RS,3SR)-β-methyltryptophan methyl ester；β-methyltryptophan methyl ester
• CAS: 90243-49-5；92735-76-7；92735-85-8；107081-05-0；131483-58-4
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: MODKVBLBJQCEKA-KBPLZSHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.11
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  β-methyltryptophan methyl ester, 2RS,3SR isomer 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 甲苯 、 苯 为溶剂， 反应 16.5h， 生成 (1S,3R,4S)-1-Isobutyl-4-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereospecific Synthesis of trans, cis-1,3,4-Trisubstituted 1,2,3,4-Tetrahydro-b-Carbolines

  摘要：

  Pictet-Spengler condensation of N(bb)-benzyl-beta-methyltryptophan methyl ester (2RS,3SR;4) with aldehydes followed by debenzylation afforded trans, cis-1,3,4-trisubstituted 1,2,3,4-tetrahydro-beta-carbolines in complete stereospecific fashion. Tetrahydro-beta-carbolines (6a) and (6b) were prepared by the direct condensation of beta-methyltryptophan methyl ester (4) with the corresponding aldehydes. The stereochemistry of the products was confirmed by an X-ray analysis of 6a.

  DOI：

  10.3987/com-91-5912
• 作为产物：
  描述：

  alpha-甲基-N-(1-甲基乙基)-1H-吲哚-3-甲胺 在 镍 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 甲苯 为溶剂， 25.0~105.0 ℃ 、275.79 kPa 条件下， 反应 11.75h， 生成 β-methyltryptophan methyl ester, 2RS,3SR isomer
  参考文献：
  名称：

  Behforouz, Mohammad; Zarrinmayeh, Hamideh; Ogle, Mark E., Journal of Heterocyclic Chemistry, 1988, vol. 25, # 6, p. 1627 - 1632

  摘要：

  DOI：

文献信息

• [EN] AMINE COMPOUNDS<br/>[FR] DERIVES D'INDOLE SERVANT D'ANTAGONISTE DE SOMATOSTATINE
  申请人：TAKEDA CHEMICAL INDUSTRIES LTD

  公开号：WO2004046107A1

  公开（公告）日：2004-06-03

  The present invention provide a compound of the formula (I) wherein ring A represents an aromatic ring optionally having substituents; B, Y and Ya are the same or different and each represents a bond, etc.; R1 and R2 are the same or different and each represents a hydrogen atom, etc.; R3 represents a hydrogen atom, etc.; R4 and R5 are the same or different and each represents a hydrogen, etc.; R6 represents an indolyl group optionally having substituents; and Z and Za are the same or different and each represents a hydrogen atom, etc.; or a salt thereof or a prodrug thereof, having a somatostatin receptor binding inhibition activity and is useful for preventing and/or treating diseases associated with somatostatin.

  本发明提供了一种公式(I)的化合物，其中环A代表一个具有可选取代基的芳香环；B、Y和Ya相同或不同，分别代表一个键等；R1和R2相同或不同，每个代表一个氢原子等；R3代表一个氢原子等；R4和R5相同或不同，每个代表一个氢等；R6代表一个可选有取代基的吲哚基团；Z和Za相同或不同，每个代表一个氢原子等；或其盐或前药，具有生长抑素受体结合抑制活性，并且用于预防或治疗与生长抑素相关的疾病。
• Short synthesis of tryptophane and β-carboline derivatives by reaction of indoles with<i>N</i>-(diphenylmethylene)-α,β-didehydroamino acid esters
  作者：Gilberto Spadoni、Cesarino Balsamini、Annalida Bedini、Ermanno Duranti、Andrea Tontini

  DOI：10.1002/jhet.5570290205

  日期：1992.3

  The ethylaluminum dichloride catalyzed Michael-type addition of indoles 1a-h to the N-(diphenylmethylene)-α,β-didehydroamino acid esters 2a-c allows a new synthesis of β-methyltryptophanes 41,m and a new route for 1,1-diphenyl-3-carbalkoxy-1,2,3,4-tetrahydro-β-carbolines 5a-m.

  二氯化乙基铝催化吲哚1a-h与N-（二苯基亚甲基）-α，β-二氢化氢氨基酸酯2a-c的Michael型加成反应使得β-甲基色氨酸41，m的新合成和1,1的新途径成为可能-二苯基-3-碳烷氧基-1,2,3,4-四氢-β-咔啉5a-m。
• A Formal Synthesis of Lavendamycin Methyl Ester, Nitramarine, and Their Analogues: A Povarov Approach
  作者：Subburethinam Ramesh、Rajagopal Nagarajan

  DOI：10.1021/jo302389s

  日期：2013.1.18

  A convergent formal synthesis of lavendamycin methyl ester and synthesis of its analogues have been delineated through the Povarov approach. This protocol is also applied to the formal synthesis of nitramarine (3) in good yield.

  通过Povarov方法已经确定了拉文霉素甲酯的收敛形式合成及其类似物的合成。该方案也适用于以高收率的形式正式合成硝胺林（3）。
• Synthesis and evaluation of antitumor activity of novel N-acyllavendamycin analogues and quinoline-5,8-diones
  作者：Mohammad Behforouz、Wen Cai、Farahnaz Mohammadi、Mark G. Stocksdale、Zhengxiang Gu、Mohammad Ahmadian、Darric E. Baty、Michele R. Etling、Charmaine H. Al-Anzi、Tyson M. Swiftney

  DOI：10.1016/j.bmc.2006.09.039

  日期：2007.1.1

  A series of 7-N-acyllavendamycins with zero, one or two substituents at the C-2', C-3', and C-11' were synthesized through short and efficient methods. Pictet-Spengler condensation of 7-N-acylamino-2-formylquinoline-5,8-diones with tryptamine or tryptophans produced the desired lavendamycins. Screening data on a panel of three ras oncogene-transformed cell lines and the non-transformed parent cell line showed that a significant number of these analogues are potent antitumor agents and appear to be particularly active against K-ras transformed cells. Compared with the corresponding quinolinediones, these novel lavendamycins are much more inhibitory toward the transformed cells indicating that the P-carboline moiety of the lavendamycin analogues plays an important role in its potency and selective toxicity. (c) 2006 Elsevier Ltd. All rights reserved.