alpha-甲基-D-色氨酸 | 56452-52-9

• 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
• 中文名称: alpha-甲基-D-色氨酸
• 中文别名: α-甲基-D-色氨酸；Α-甲基-D-色氨酸
• 英文名称: α-methyl-DL-tryptophan
• 英文别名: α-methyl-D-tryptophan；L-α-methyltryptophan；DL-α-methyltryptophan；(2R)-2-azaniumyl-3-(1H-indol-3-yl)-2-methylpropanoate
• CAS: 56452-52-9
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: ZTTWHZHBPDYSQB-GFCCVEGCSA-N

物化性质

• 沸点：
  444.0±35.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  9-(chloromethyl)fluorene 、 alpha-甲基-D-色氨酸 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以96%的产率得到
  参考文献：
  名称：

  The stereocontrolled synthesis of orthogonally protected (R)-α-methyltryptophan

  摘要：

  An expedient and highly stereocontrolled route to (R)-alpha-methyltryptophan and its orthogonally protected analogs has been developed via a four-step conversion from L-alanine in good overall yields. The stereochemistry of the products is confirmed by X-ray diffraction analysis, NMR spectroscopy and optical rotations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02302-8
• 作为产物：
  描述：

  N-苄氧羰基-D-色氨酸 在 palladium on activated charcoal 氢气 、 sodium carbonate 、 caesium carbonate 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 109.5h， 生成 alpha-甲基-D-色氨酸
  参考文献：
  名称：

  Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in enantiospecific preparation of α-methyltryptophan: application in the preparation of carbon-14 labeled PD 145942 and PD 154075

  摘要：

  [2R-(2 alpha, 3a beta, 8a beta)]-2,3,3a,8a-Tetrahydro-pyrrolo[2.3-b]indole-1,2,8-tricarboxylic acid-1,8-dibenzyl ester 2-methyl ester, its [2S-(2 beta, 3a alpha, 8a alpha)]-isomer, and the tribenzyl ester analogs were prepared. From these [2,3-b]indole-1,2,8-tricarboxylic acid esters we accomplished a simple, high yielding preparation of enantiopure alpha-methyltryptophan and methyl ester derivatives. Using this protocol, we inexpensively made (R)-alpha-[C-14]methyltryptophan methyl ester, and in subsequent reactions converted it into [1-(2-hydroxy-cyclohexylcarbamoyl)-2-(1H-indol-3-yl)-1-[C-14]methylethyl]carbamic acid adamantan-2-yl ester (PD 145942) and [2-(1H-indole-3-yl)-1-[C-14]methyl-1(1-phenyl-ethylcarbamoyl)-ethyl]carbamic acid benzofuran-2-yl methyl ester (PD 154075). Both of these compounds are drug candidates in preclinical study for the treatment of anxiety and emesis respectively.

  DOI：

  10.1002/(sici)1099-1344(199712)39:12<1019::aid-jlcr43>3.0.co;2-t

文献信息

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2018006063A1

  公开（公告）日：2018-01-04

  Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

  用于治疗细菌感染的组合物和方法包括含有环七肽二聚体与一个或多个单糖或寡糖基团结合的化合物。特别是，这些化合物可用于治疗由革兰氏阴性细菌引起的细菌感染。
• N-substituted cycloalkyl and polycycloalkyl alpha-substituted Trp-Phe-
  申请人：Warner-Lambert Company

  公开号：US05278316A1

  公开（公告）日：1994-01-11

  Novel unnatural dipeptoids of .alpha.-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, or as antipsychotics are disclosed. Further the compounds are antianxiety agents, antiulcer agents, antidepressant agents, and are agents useful for preventing the withdrawal response produced by chronic treatment or use followed by chronic treatment followed by withdrawal from nicotine, diazepam, alcohol, cocaine, caffeine, or opiods. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare pharmaceutical and diagnostic compositions.

  揭示了作为治疗肥胖、肠道胃酸过多、胃泌素依赖性肿瘤或抗精神病药物的α-取代Trp-Phe衍生物的新型非天然二肽类化合物。此外，这些化合物还是抗焦虑剂、抗溃疡剂、抗抑郁剂，并且可用作预防慢性治疗或使用后随之慢性治疗再随之戒断尼古丁、安定、酒精、可卡因、咖啡因或阿片类药物所产生的戒断反应的药物。还公开了使用这些二肽类化合物的药物组合物和治疗方法，以及用于制备它们的过程和在其制备中有用的新型中间体。该发明的另一个特点是使用这些化合物制备药物和诊断组合物。
• [EN] PEPTIDE-BASED MULTIPLE-DRUG DELIVERY VEHICLE<br/>[FR] VÉHICULE D'ADMINISTRATION DE MÉDICAMENTS MULTIPLES À BASE DE PEPTIDES
  申请人：ARIEL-UNIVERSITY RES AND DEV COMPANY LTD

  公开号：WO2017068577A1

  公开（公告）日：2017-04-27

  A molecular structure comprising a targeting moiety, a multi-functional peptide platform and a plurality of controllably released bioactive agents attached thereto is provided herein.

  本文提供了一种包括靶向基团、多功能肽平台和附着在其上的多种可控释放的生物活性剂的分子结构。
• Novel eicosanoid derivatives
  申请人：Max-Delbrück-Centrum für Molekulare Medizin (MDC)

  公开号：EP2208720A1

  公开（公告）日：2010-07-21

  The present invention provides compounds (n-3 PUFA derivatives) of formula (I): that modulate conditions associated with cardiac damage, especially cardiac arrhythmias.

  本发明提供了式(I)的化合物（n-3 PUFA衍生物）： 这些化合物调节与心脏损伤相关的病症，特别是心律失常。
• N-substituted cycloalkyl and polycycloalkyl .alpha.-substituted Trp-Phe-
  申请人：Warner-Lambert Company

  公开号：US05631281A1

  公开（公告）日：1997-05-20

  Novel unnatural dipeptoids of .alpha.-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, colorectal tumors, or as antipsychotics are disclosed. Further the compounds are antianxiety agents, antiulcer agents, antidepressant agents, and are agents useful for preventing the withdrawal response produced by chronic treatment or use followed by chronic treatment followed by withdrawal from nicotine, diazepam, alcohol, cocaine, caffeine, or opiods. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare pharmaceutical and diagnostic compositions.

  揭示了作为治疗肥胖、肠道胃酸过多、胃泌素依赖性肿瘤、结肠肿瘤或抗精神病药物的α-取代Trp-Phe衍生物的新型非天然二肽类化合物。此外，这些化合物还是抗焦虑剂、抗溃疡剂、抗抑郁剂，并且可用作预防慢性治疗或使用后的戒断反应，包括尼古丁、安定、酒精、可卡因、咖啡因或阿片类药物的慢性治疗后随后的戒断反应。还公开了使用这些二肽类化合物的药物组合物和治疗方法，以及用于制备它们的过程和在其制备中有用的新型中间体。该发明的另一个特点是使用这些化合物来制备药物和诊断组合物。