N_a-methyl tryptophan methyl ester | 7638-53-1

• 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: N_a-methyl tryptophan methyl ester
• 英文别名: N_a-methyltryptophan methyl ester；methyl 1-methyltryptophanate；dl-1-Methyl-tryptophan-methylester；1-Methyl-tryptophan-methylester；1-Methyl-tryptophanmethylester；Methyl 2-amino-3-(1-methylindol-3-yl)propanoate
• CAS: 7638-53-1
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: KMSKYVDBQZIXDU-UHFFFAOYSA-N

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：
  0.31
• 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：

  N_a-methyl tryptophan methyl ester 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 30.0h， 生成 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid
  参考文献：
  名称：

  Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids

  摘要：

  DOI：

  10.1021/ja00342a045
• 作为产物：
  描述：

  芦竹碱 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 氯化亚砜 、 溶剂黄146 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 为溶剂， 生成 N_a-methyl tryptophan methyl ester
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077

文献信息

• [EN] IMIDAZOLE DERIVATIVES AS IDO INHIBITORS<br/>[FR] DÉRIVÉS IMIDAZOLE COMME INHIBITEURS DE L'IDO
  申请人：NEWLINK GENETICS

  公开号：WO2011056652A1

  公开（公告）日：2011-05-12

  Presently provided are IDO inhibitors of general formulae (VII), (VIII) as shown below and pharmaceutical compositions thereof, useful for modulating an activity of indoleamine 2,3-dioxygenase; treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression; treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase; enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent; treating tumor-specific immunosuppression associated with cancer; and treating immunosupression associated with an infectious disease.

  目前提供的是通用结构式（VII）、（VIII）所示的IDO抑制剂及其药物组合物，用于调节色胺酸2,3-二氧化酶的活性；治疗色胺酸2,3-二氧化酶（IDO）介导的免疫抑制；治疗受益于色胺酸-2,3-二氧化酶酶活性抑制的医疗状况；增强包括给予抗癌药物在内的抗癌治疗的有效性；治疗与癌症相关的肿瘤特异性免疫抑制；以及治疗与传染性疾病相关的免疫抑制。
• MITHRAMYCIN OXIME AND HYDRAZINE DERIVATIVES HAVING INCREASED SELECTIVITY AND ANTI-CANCER ACTIVITY
  申请人：University of Kentucky Research Foundation

  公开号：US20200131218A1

  公开（公告）日：2020-04-30

  Compounds described herein are mithramycin (MTM) oxide (OX) derivatives and MTM Hydrazine (HY) derivatives. These compounds are useful for treatment of cancers and neuro-diseases.

  本文描述的化合物是米司雷霉素（MTM）氧化物（OX）衍生物和MTM肼（HY）衍生物。这些化合物对于治疗癌症和神经疾病非常有用。
• SALTS AND PRODRUGS OF 1-METHYL-D-TRYPTOPHAN
  申请人：NewLink Genetics, Corp.

  公开号：US20170022157A1

  公开（公告）日：2017-01-26

  Presently provided are indoximod prodrug and salt compounds and pharmaceutical compositions comprising salts and prodrugs of indoximod, that produce enhanced plasma concentration and exposure to indoximod compared to direct administration of indoximod, in patients in need of treatment of immunosuppression mediated by the indoleamine-2,3-dioxygenase pathway, such as patients with cancer or chronic infectious diseases.

  目前提供的是吲哚氧化酶抑制剂前药和盐类化合物，以及包含吲哚氧化酶抑制剂前药和盐类的药物组合物，相比直接给予吲哚氧化酶抑制剂，这些组合物在需要治疗由吲哚胺-2,3-二氧化酶途径介导的免疫抑制的患者中，如癌症或慢性传染病患者，能够产生增强的血浆浓度和暴露于吲哚氧化酶抑制剂。
• Wittig Reactions of Maleimide-Derived Stabilized Ylides with Alkyl Pyruvates: Concise Approach to Methyl Ester of (±)-Chaetogline A
  作者：Narshinha P. Argade、Santosh V. Shelar

  DOI：10.1055/a-1477-6043

  日期：2021.8

  facile synthesis of methyl ester of chaetogline A is reported starting from the corresponding methyl 1-methyltryptophanate-derived­ maleimide. A stereoselective Wittig olefination with a carbonyl function in methyl pyruvate followed by phosphorous pentoxide-induced­ regioselective dehydrative cyclization are the essential reactions. An acid-induced thermodynamically driven stereoselective β- to α-position

  据报道，从相应的1-甲基色氨酸甲酯衍生的马来酰亚胺开始，容易合成chaetogline A的甲酯。丙酮酸甲酯中具有羰基官能团的立体选择性维蒂希烯化反应，然后由五氧化二磷诱导的区域选择性脱水环化反应是必不可少的反应。描述了酸诱导的热力学驱动的四氢吲哚并吲哚亚丙基亚丙基乙酯中环外C = C键单元的立体选择性β-至α-位迁移。
• Imidazole Derivatives as IDO Inhibitors
  申请人：Mautino Mario R.

  公开号：US20120277217A1

  公开（公告）日：2012-11-01

  Presently provided are IDO inhibitors of general formulae (VII), (VIII) as shown below and pharmaceutical compositions thereof, useful for modulating an activity of indoleamine 2,3-dioxygenase; treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression; treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase; enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent; treating tumor-specific immunosuppression associated with cancer; and treating immunosupression associated with an infectious disease.

  目前提供的是通式（VII），（VIII）所示的IDO抑制剂及其制药组合物，用于调节吲哚胺2,3-二氧化酶的活性；治疗由吲哚胺2,3-二氧化酶（IDO）介导的免疫抑制；治疗受益于抑制吲哚胺2,3-二氧化酶酶活性的医疗状况；增强包括给予抗癌药物在内的抗癌治疗的有效性；治疗与癌症相关的肿瘤特异性免疫抑制；以及治疗与传染病相关的免疫抑制。