(R)-2-Amino-3-(3-methyl-3H-imidazol-4-yl)-propionic acid methyl ester | 221333-63-7

• 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: (R)-2-Amino-3-(3-methyl-3H-imidazol-4-yl)-propionic acid methyl ester
• 英文别名: methyl (2R)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoate；methyl (2R)-2-amino-3-(3-methylimidazol-4-yl)propanoate
• CAS: 221333-63-7
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: KSVGMEHIGJQRQB-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-3-(3-methyl-3H-imidazol-4-yl)-propionic acid methyl ester 在 lithium hydroxide 、 sodium cyanoborohydride 作用下， 生成 1-[(2R)-2-[(4-cyanobenzyl)(methyl)amino]-3-(1-methyl-1H-imidazol-5-yl)propanoyl]-5-(1-naphthyl)-1,2,3,6-tetrahydropyridine-4-carbonitrile
  参考文献：
  名称：

  Aryl tetrahydropyridine inhibitors of farnesyltransferase: glycine, phenylalanine and histidine derivatives

  摘要：

  Inhibitors of farnesyltransferase are effective against a variety of tumors in mouse models of cancer. Clinical trials to evaluate these agents in humans are ongoing. In our effort to develop new farnesyltransferase inhibitors, we have discovered a series of aryl tetrahydropyridines that incorporate substituted glycine, phenylalanine and histidine residues. The design, synthesis, SAR and biological properties of these compounds will be discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00095-7
• 作为产物：
  描述：

  (5S,10aS)-9-<<5-<(2S-trans)-2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)pyrazin-5-yl>methyl-1-methyl-1H-imidazol-4-yl>thio>-6,8-dimethoxy-5-<(4-methoxyphenyl)methyl>-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one 在 镍 盐酸 、 甲醇 作用下， 以 甲醇 为溶剂， 反应 9.5h， 生成 (R)-2-Amino-3-(3-methyl-3H-imidazol-4-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthetic Studies on the Starfish Alkaloid Imbricatine. Construction of an ent-Imbricatine Framework.

  摘要：

  作为海星生物碱 imbricatine（3）全合成的前奏，我们开发出了含有 ent-imbricatine（ent-3）基本框架的氨基酯 5 和 6 的手性合成路线。该路线从含硫 L-苯丙氨酸衍生物 7 开始，经过无外消旋化的环化酰胺 8、还原为 1，3-顺式四氢异喹啉 9，以及通过 "双内酯醚 "法将手性 α-氨基酸分子引入氯化物 18 等关键步骤。

  DOI：

  10.1248/cpb.47.83

文献信息

• Aryl tetrahydropyridine inhibitors of farnesyltransferase: glycine, phenylalanine and histidine derivatives
  作者：Stephen L. Gwaltney、Stephen J. O'Connor、Lissa T.J. Nelson、Gerard M. Sullivan、Hovis Imade、Weibo Wang、Lisa Hasvold、Qun Li、Jerome Cohen、Wen-Zhen Gu、Stephen K. Tahir、Joy Bauch、Kennan Marsh、Shi-Chung Ng、David J. Frost、Haiying Zhang、Steve Muchmore、Clarissa G. Jakob、Vincent Stoll、Charles Hutchins、Saul H. Rosenberg、Hing L. Sham

  DOI：10.1016/s0960-894x(03)00095-7

  日期：2003.4

  Inhibitors of farnesyltransferase are effective against a variety of tumors in mouse models of cancer. Clinical trials to evaluate these agents in humans are ongoing. In our effort to develop new farnesyltransferase inhibitors, we have discovered a series of aryl tetrahydropyridines that incorporate substituted glycine, phenylalanine and histidine residues. The design, synthesis, SAR and biological properties of these compounds will be discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthetic Studies on the Starfish Alkaloid Imbricatine. Construction of an ent-Imbricatine Framework.
  作者：Masashi OHBA、Masaaki IMASHO、Tozo FUJII

  DOI：10.1248/cpb.47.83

  日期：——

  A chiral synthetic route to the amino esters 5 and 6, which contain the fundamental framework of ent-imbricatine (ent-3), has been developed as a prelude to the total synthesis of the starfish alkaloid imbricatine (3). The route started from the sulfur-containing L-phenylalanine derivative 7 and proceeded through key steps such as cyclization fo the amide 8 without racemization, reduction to the 1, 3-cis-tetrahydroisoquinoline 9, and introduction of a chiral α-amino acid moiety into the chloride 18 by the "bis-lactim ether" method.

  作为海星生物碱 imbricatine（3）全合成的前奏，我们开发出了含有 ent-imbricatine（ent-3）基本框架的氨基酯 5 和 6 的手性合成路线。该路线从含硫 L-苯丙氨酸衍生物 7 开始，经过无外消旋化的环化酰胺 8、还原为 1，3-顺式四氢异喹啉 9，以及通过 "双内酯醚 "法将手性 α-氨基酸分子引入氯化物 18 等关键步骤。