S-(-)-methyl 2-α[N-t-butoxycarbonyl]aminopropionyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate | 320589-57-9

• 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: S-(-)-methyl 2-α[N-t-butoxycarbonyl]aminopropionyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: methyl (3S,2'S)-1,2,3,4-tetrahydro-2-N'-tert-butoxycarbonylalanyl-β-carboline-3-carboxylate；(3S)-2-(Boc-L-alanyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester；3S-2-(Boc-L-alanyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester；methyl (3S)-2-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• CAS: 320589-57-9
• 化学式: C₂₁H₂₇N₃O₅
• 分子量: 401.462
• InChiKey: NJTDVNWIKHYFRC-SJCJKPOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-(-)-methyl 2-α[N-t-butoxycarbonyl]aminopropionyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 在 sodium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (5S,8S)-7-ethoxy-5-methyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),6,11,13,15-pentaen-4-one
  参考文献：
  名称：

  The fate of the tryptophan stereocenter in the synthesis of 7,10,16,16a-tetrahydro-11H-quinazolino[2′,3′:3,4]pyrazino[1,2-b]β-carboline-5,8-diones

  摘要：

  Condensation reactions of anthranilic acid with iminoethers 14-17 derived from tetracycles 9-13 to give the title hexacyclic compounds reflect a preferred trans-relationship for H(10)-H(16a) protons in C(7)-unsubstituted products and a cis-relatioship for H(7)-H(16a) protons in C(10)-unsubstituted analogs. This synthetic strategy is limited by the steric hindrance of the substituent at C(10). Theoretical calculations are in agreement with the experimental results. The regioselectivity in favor of the linear tetracyclic compound 11 with respect to 12 has also been confirmed. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00282-2
• 作为产物：
  描述：

  (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 在 氯化亚砜 、 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 S-(-)-methyl 2-α[N-t-butoxycarbonyl]aminopropionyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Toward breast cancer resistance protein (BCRP) inhibitors: design, synthesis of a series of new simplified fumitremorgin C analogues

  摘要：

  In this study, we report the design and synthesis of a series of new simplified fumitremorgin C analogues. The preliminary biological study indicated some of these simplified fumitremorgin C might be developed into breast cancer resistance inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.045

文献信息

• Microwave assisted stereospecific synthesis of (S)-3-substituted 2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-diones
  作者：Suresh K Pandey、Keshav K Awasthi、Anil K Saxena

  DOI：10.1016/s0040-4020(01)00334-9

  日期：2001.5

  A new easy way of preparing (S)-3-substituted 2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-diones, an important intermediate compound, is described using microwave irradiation supported on silica gel. The reaction is generalised and good to excellent yields of enantiomerically pure products are obtained.

  一种制备（S）-3-取代的2,3,6,7,12,12a-六氢吡嗪并[1'，2'：1,6]吡啶[3,4- b ]吲哚-1,4的简便方法使用载于硅胶上的微波辐射描述了重要的中间体化合物-二酮。反应被普遍进行，并且获得对映体纯产物的良好至极好的收率。
• A Class of 3<i>S</i>-2-Aminoacyltetrahydro-β-carboline-3-carboxylic Acids: Their Facile Synthesis, Inhibition for Platelet Activation, and High in Vivo Anti-Thrombotic Potency
  作者：Jiawang Liu、Xueyun Jiang、Ming Zhao、Xiaoyi Zhang、Meiqing Zheng、Li Peng、Shiqi Peng

  DOI：10.1021/jm901816j

  日期：2010.4.22

  3S-Tetrahydro-beta-carboline-3-carboxylic acid (TCCA) effectively inhibits ADP-induced platelet activation. This paper used TCCA as a lead, modified its 2-position with amino acids, and provided 20 novel 3S-2-aminoacyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acids (5a-t). With the in vitro assay, it was demonstrated that this modification diminished the IC(50) values from 701 nM of TCCA to 10 nM of 5a-t. With the in vivo assay, it was demonstrated that this modification reduced the efficacious dose from 5.0 mu mol/kg of TCCA to 0.1 mu mol/kg of 5a-t. Comparing the Cerius(2) based conformation of them with that of their analogues, the 3-position modified TCCA, it was suggested that the comparatively unfolded conformation was one of the important factors of enhancing the in vivo antithrombotic potency.
• Toward breast cancer resistance protein (BCRP) inhibitors: design, synthesis of a series of new simplified fumitremorgin C analogues
  作者：Guofeng Wu、Jiawang Liu、Lanrong Bi、Ming Zhao、Chao Wang、Michèle Baudy-Floc'h、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.tet.2007.04.045

  日期：2007.6

  In this study, we report the design and synthesis of a series of new simplified fumitremorgin C analogues. The preliminary biological study indicated some of these simplified fumitremorgin C might be developed into breast cancer resistance inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.
• The fate of the tryptophan stereocenter in the synthesis of 7,10,16,16a-tetrahydro-11H-quinazolino[2′,3′:3,4]pyrazino[1,2-b]β-carboline-5,8-diones
  作者：Antonio Madrigal、Mercedes Grande、Carmen Avendaño

  DOI：10.1016/s0957-4166(00)00282-2

  日期：2000.9

  Condensation reactions of anthranilic acid with iminoethers 14-17 derived from tetracycles 9-13 to give the title hexacyclic compounds reflect a preferred trans-relationship for H(10)-H(16a) protons in C(7)-unsubstituted products and a cis-relatioship for H(7)-H(16a) protons in C(10)-unsubstituted analogs. This synthetic strategy is limited by the steric hindrance of the substituent at C(10). Theoretical calculations are in agreement with the experimental results. The regioselectivity in favor of the linear tetracyclic compound 11 with respect to 12 has also been confirmed. (C) 2000 Published by Elsevier Science Ltd.