3-(2-氨基-4-噻唑基)丙酸甲酯 | 398472-21-4

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(2-氨基-4-噻唑基)丙酸甲酯
• 中文别名: 3-(2-氨基-1,3-噻唑-4-基)丙酸甲酯
• 英文名称: methyl 3-(2-amino-4-thiazolyl)propionate
• 英文别名: 3-(2-amino-thiazol-4-yl)-propionic acid methyl ester；3-(2-Amino-thiazol-4-yl)-propionsaeure-methylester；Methyl-β-(2-amino-4-thiazolyl)propionat；Methyl 3-(2-amino-1,3-thiazol-4-yl)propanoate
• CAS: 398472-21-4
• 化学式: C₇H₁₀N₂O₂S
• mdl: MFCD01415011
• 分子量: 186.235
• InChiKey: JWDGXHZFNYKFGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-氨基-4-噻唑基)丙酸甲酯 在 甲醇 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 isopropyl (2'-methyl-5-(3-(2-(tritylamino)thiazol-4-yl)propanamido)-[1,1'-biphenyl]-2-carbonyl)-L-methioninate
  参考文献：
  名称：

  Thiazole- and imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase

  摘要：

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed replacing internal dipeptide AA with 4-amino-2-phenylbenzoic acid and cysteine (C) with 2-amino-4-thiazolyl-, 2-mercapto-4-thiazolyl-, 2-mercapto-4-imidazolyl- and 2-methylmercapto-4-thiazolyl-acetic or propionic acid. The compound in which C is replaced by 2-amino-4-thiazolylacetic acid inhibited FTase activity in the low nanomolar range and showed antiproliferative effect on rat aortic smooth muscle cells interfering with Ras farnesylation. On the basis of these results, 2-aminothiazole can be considered as an alternative to heterocycles, such as pyridine and imidazole, normally used in FTase inhibitors designed as non-thiol CAAX mimetics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.003
• 作为产物：
  描述：

  丁二酸单甲酯酰氯 在 乙醚 、 乙醇 作用下， 生成 3-(2-氨基-4-噻唑基)丙酸甲酯
  参考文献：
  名称：

  δ-琥珀酰胺基果酸及其相关化合物的合成

  摘要：

  DOI：

  10.1039/jr9540001820
• 作为试剂：
  描述：

  1-cyclohexylmethyl-2-oxo-1,2,5,6,7,8,9,10-octahydro-cycloocta[b]pyridine-3-carboxylic acid 、 3-(2-氨基-4-噻唑基)丙酸甲酯 在 3-(2-氨基-4-噻唑基)丙酸甲酯 作用下， 生成 methyl 3-(2-(1-(cyclohexylmethyl)-2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamido)thiazol-4-yl)propanoate
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 2012, 22, 2898-2901

  摘要：

  DOI：

文献信息

• Rappe, Arkiv foer Kemi, 1959, vol. 14, p. 467,471
  作者：Rappe

  DOI：——

  日期：——
• Thiazole- and imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase
  作者：Cristiano Bolchi、Marco Pallavicini、Sergio K. Bernini、Giuseppe Chiodini、Alberto Corsini、Nicola Ferri、Laura Fumagalli、Valentina Straniero、Ermanno Valoti

  DOI：10.1016/j.bmcl.2011.07.003

  日期：2011.9

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed replacing internal dipeptide AA with 4-amino-2-phenylbenzoic acid and cysteine (C) with 2-amino-4-thiazolyl-, 2-mercapto-4-thiazolyl-, 2-mercapto-4-imidazolyl- and 2-methylmercapto-4-thiazolyl-acetic or propionic acid. The compound in which C is replaced by 2-amino-4-thiazolylacetic acid inhibited FTase activity in the low nanomolar range and showed antiproliferative effect on rat aortic smooth muscle cells interfering with Ras farnesylation. On the basis of these results, 2-aminothiazole can be considered as an alternative to heterocycles, such as pyridine and imidazole, normally used in FTase inhibitors designed as non-thiol CAAX mimetics. (C) 2011 Elsevier Ltd. All rights reserved.
• The synthesis of δ-succinamidolœvulic acid and related compounds
  作者：A. Neuberger、J. J. Scott

  DOI：10.1039/jr9540001820

  日期：——
• Bioorg. Med. Chem. Lett. 2012, 22, 2898-2901
  作者：

  DOI：——

  日期：——