Nα-methyl-L-histidine methyl ester

• 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: Nα-methyl-L-histidine methyl ester
• 英文别名: N-Methyl-L-histidine methyl ester；Me-His-OMe；(S)-Methyl 3-(1H-imidazol-5-yl)-2-(methylamino)propanoate；methyl (2S)-3-(1H-imidazol-5-yl)-2-(methylamino)propanoate
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: BHLAPZWOGGWVRR-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲氧羰酰琥珀酰亚胺 、 Nα-methyl-L-histidine methyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以88%的产率得到Cbz-MeHis(Cbz)-OMe
  参考文献：
  名称：

  Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase

  摘要：

  Arylboronic acid based technology provides a mild, regioselective, and nontoxic N-arylation procedure for accessing the Unusual N-arylated side chain histidine found in the active site of cytochrome c oxidase (CcO) The N-arylated histidine is elaborated to the complete cytochrome c oxidase cyclic pentapeptide cofactor. Molecular modeling of the cofactor provides insight into the dynamic character of the N-aryl bond.

  DOI：

  10.1021/jo901744y
• 作为产物：
  描述：

  N-甲基-L-组氨酸 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 Nα-methyl-L-histidine methyl ester
  参考文献：
  名称：

  Intermediates in polypeptide synthesis

  摘要：

  苯丙氨酰组氨酸的双(叔丁氧羰基)衍生物作为合成抑制凝乳酶多肽的中间体。

  公开号：

  US04599198A1

文献信息

• Novel amino acid derivatives possessing renin-inhibitory activities
  申请人：Japan Tobacco Inc.

  公开号：EP0396065A1

  公开（公告）日：1990-11-07

  An amino acid derivative of the general formula: wherein R1 is wherein, R10 is a lower alkyl group and R" is (wherein R111 is a lower alkyl group and n is an integer of 1 to 5) or a lower alkyl group which may be substituted by hydroxy group or methoxyethoxymethoxy group, or R'° and R" are combinedly together with the adjacent nitrogen atom; R12 is a hydrogen atom, CnH2n+1-O-CO- (n is as defined above) or R'3 is a lower alkyl group which may be substituted by substituent(s) selected from HOOC-(H2C)n-O-, R12- NH- (n and R12 are as defined above) and pyridyl group; X is -CH2-, -O- or -NH- and Y is -O- or -NH-; wherein (wherein Z is -0-, -S-, -S(O)-. -S(O)2-, -CH2-, -CH(OH)-, or and a and b are independently an integer of 1 to 4 and the total of a and b is not more than 5) ; R2 is an aralkyl group which may be substituted by lower alkyl group(s); R3 is a hydrogen atom or a lower alkyl group; R4 is a lower alkyl group; and A is hydroxy group and B is a hydrogen atom, or A and B are carbonyl group combinedly together with the adjacent carbon atom, a pharmaceutically acceptable acid addition salt or an ester thereof is described. The compounds of the invention possess inhibitory activities against renin and are useful as an antihypertensive agent.

  通用公式的氨基酸衍生物： 其中R1为 其中，R10为较低的烷基基团，R"为 （其中R111为较低的烷基基团，n为1至5的整数）或者可以被羟基或甲氧乙氧甲氧基取代的较低烷基基团，或者R'°和R"与相邻的氮原子 结合在一起； R12为氢原子，CnH2n+1-O-CO-（n如上定义）或者 R'3为可以被HOOC-(H2C)n-O-、R12-NH-（n和R12如上定义）和吡啶基取代的较低烷基基团； X为-CH2-、-O-或-NH-，Y为-O-或-NH-；其中 （其中Z为-0-、-S-、-S(O)-、-S(O)2-、-CH2-、-CH(OH)-， 或 a和b分别独立为1至4的整数，且a和b的总和不超过5）； R2为可以被较低烷基基团取代的芳基烷基基团； R3为氢原子或较低烷基基团； R4为较低烷基基团； A为羟基，B为氢原子，或者A和B与相邻的碳原子结合在一起，描述了一种药学上可接受的酸盐或其酯。本发明的化合物具有对肾素的抑制活性，并可用作降压药。
• Facile Synthesis of Highly Functionalized <i>N-</i>Methyl Amino Acid Esters without Side-Chain Protection
  作者：Kimberly N. White、Joseph P. Konopelski

  DOI：10.1021/ol051441w

  日期：2005.9.1

  [reaction: see text] The facile, two-pot synthesis of N-methyl amino acid esters by way of reductive amination is presented. Side chain protection schemes are not required, the starting materials are all commercially available, and the synthetic method is straightforward and affords desired product in very high yield.

  [反应：见正文]提出了一种通过还原胺化的简便，两锅法合成N-甲基氨基酸酯的方法。不需要侧链保护方案，起始原料都是可商购的，并且合成方法是直接的并且可以非常高的产率提供所需的产物。
• NOVEL HISTIDINE DERIVATIVES
  申请人：Nakazawa Yoshitaka

  公开号：US20100152459A1

  公开（公告）日：2010-06-17

  The present invention is to provide a novel compound which is useful as a pharmaceutical agent such as an analgesic. The present invention is to provide the novel histidine derivative having an excellent analgesic action and the like. The compound of the present invention has a very high intermigration into the blood upon oral administration and is very useful as a pharmaceutical agent, especially an analgesic for the treatment of acute or chronic pain diseases and of neuropathic pain diseases.

  本发明提供了一种新型化合物，可用作药物剂，如镇痛剂。本发明提供了具有出色镇痛作用的新型组氨酸衍生物等。本发明的化合物在口服后能够迅速进入血液循环，并且非常适用作为药物剂，特别是用于治疗急性或慢性疼痛疾病和神经病理性疼痛疾病的镇痛剂。
• Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4
  申请人：ELAN PHARMACEUTICALS, INC.

  公开号：EP1612215A1

  公开（公告）日：2006-01-04

  Disclosed are pyroglutamic acid derivatives and related compounds which bind VLA-4. Certain of these compounds also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g. human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本文披露了与VLA-4结合的吡咯烷酸衍生物和相关化合物。其中某些化合物还抑制白细胞粘附，特别是通过VLA-4介导的白细胞粘附。这些化合物在治疗哺乳动物患者（例如人类）的炎症性疾病中非常有用，如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎症性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。
• 3-(Heteroaryal) alanine derivatives-inhibitors of leukocyte adhesion mediated by VLA-4
  申请人：——

  公开号：US20020052375A1

  公开（公告）日：2002-05-02

  Disclosed are certain 3-(heteroaryl)alanine derivatives which bind VLA-4 and inhibit leukocyte adhesion mediated by VLA-4. Such compounds are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The compounds can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

  本发明涉及某些3-(杂环芳基)丙氨酸衍生物，其与VLA-4结合并抑制由VLA-4介导的白细胞粘附。这些化合物可用于治疗哺乳动物患者（例如人类）的炎症性疾病，如哮喘、阿尔茨海默病、动脉粥样硬化、艾滋病痴呆、糖尿病、炎性肠病、类风湿性关节炎、组织移植、肿瘤转移和心肌缺血。这些化合物还可用于治疗多发性硬化等炎症性脑部疾病。