methyl 3-(2-mercapto-4-imidazolyl)propionate | 115785-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-(2-mercapto-4-imidazolyl)propionate
• 英文别名: Methyl 3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)propanoate
• CAS: 115785-08-5
• 化学式: C₇H₁₀N₂O₂S
• 分子量: 186.235
• InChiKey: YROZKJUFWUUCBP-UHFFFAOYSA-N

物化性质

• 沸点：
  284.5±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-mercapto-4-imidazolyl)propionate 在 sodium hydroxide 作用下， 反应 2.0h， 以72%的产率得到3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-propionic acid
  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：

  methyl 5-azidolevulinate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 6.0h， 生成 methyl 3-(2-mercapto-4-imidazolyl)propionate
  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

文献信息

• [EN] PROCESS FOR SYNTHESIZING ERGOTHIONEINE AND RELATED COMPOUNDS<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE L'ERGOTHIONÉINE ET DE COMPOSÉS APPARENTÉS
  申请人：UNIV CAPE TOWN

  公开号：WO2016046618A1

  公开（公告）日：2016-03-31

  The invention provides a process for synthesising a compound of formula (V) wherein: formula (z) or a physiologically acceptable salt, tautomer, stereoisomer or mixture of stereoisomers thereof. The process utilizes a /V-benzyl protected histidine rather than the unprotected form of histidine. The process of the invention comprises the steps of: (a) deprotecting a /V-benzyl protected histidine of formula 11 to form A/-benzyl histidine of formula 12; (b) converting compound 12 to (S)-3-(1 -benzyl-1 H-imidazol-4-yl)-2-(dimethylamino)propanoic acid of formula 13; (c) converting compound 13 to (2S)-N,N,N-2-trimethylethanaminium-3-(1 -benzyl- 1H-imidazol-4-yl)propanoic acid of formula 14; (d) brominating the imidazole ring of the compound of formula 14 to form 5-bromohercynine lactone (reactive intermediate); and (e) converting the 5-bromohercynine lactone of step (d) to (p-amino-p- carboxyethyl)ergothioneine sulfide of formula 15. The process optionally further includes one of steps (f) to (h): (f) converting the compound of formula 15 to a sulfoxide; (g) converting the compound of formula 15 to a sulfone; or (h) converting the compound of formula 15 to ergothioneine (ESH).

  本发明提供了一种合成式（V）化合物的方法，其中：公式（z）或其生理可接受的盐、变构体、立体异构体或立体异构体混合物。该方法使用/V-苄基保护组氨酸代替未保护的组氨酸。本发明的方法包括以下步骤：（a）去保护公式11的/V-苄基保护组氨酸，形成公式12的A/-苄基组氨酸；（b）将化合物12转化为公式13的（S）-3-（1-苄基-1H-咪唑-4-基）-2-（二甲氨基）丙酸；（c）将化合物13转化为公式14的（2S）-N，N，N-2-三甲基乙酰胺-3-（1-苄基-1H-咪唑-4-基）丙酸；（d）溴化公式14化合物中的咪唑环，形成5-溴赫尔岑酮（反应中间体）；和（e）将步骤（d）中的5-溴赫尔岑酮转化为公式15的（对氨基-对羧乙基）麦角硫氨酸硫醚。该方法还可选地进一步包括步骤（f）至（h）中的一项：（f）将公式15的化合物转化为亚砜；（g）将公式15的化合物转化为磺酰；或（h）将公式15的化合物转化为麦角硫氨酸（ESH）。
• NALPHA, NALPHA, NALPHA-TRIALKYL HISTIDINE DERIVATIVES USEFUL FOR THE PREPARATION OF ERGOTHIONEINE COMPOUNDS
  申请人：Mironova Innovations, LLC

  公开号：EP3268354B1

  公开（公告）日：2020-05-06
• CONDUCTIVE FILM FORMING COMPOSITION, CONDUCTIVE FILM, AND WIRING BOARD
  申请人：FUJIFILM Corporation

  公开号：US20160021741A1

  公开（公告）日：2016-01-21

  A conductive film forming composition includes a fluorine atom-containing migration inhibitor and a metal particle, with the migration inhibitor including at least one selected from the group consisting of compounds represented by General Formulae (1) to (5), (22) and (23) as well as compounds having a group of General Formula (24) and a group of General Formula (25). The conductive film forming composition makes it possible to form a conductive film excellent in conductive characteristics and ion migration inhibiting function.
• ORGANIC SEMICONDUCTOR COMPOSITION, ORGANIC THIN-FILM TRANSISTOR, ELECTRONIC PAPER, AND DISPLAY DEVICE
  申请人：FUJIFILM Corporation

  公开号：US20160071624A1

  公开（公告）日：2016-03-10

  The present invention provides an organic semiconductor composition, which improves the insulation reliability of an organic thin-film transistor without greatly reducing the mobility of the organic thin-film transistor, an organic thin-film transistor which is formed by using the organic semiconductor composition, and electronic paper and a display device which use the organic thin-film transistor. The organic semiconductor composition of the present invention contains an organic semiconductor material and an F-containing migration inhibitor selected from the group consisting of a compound represented by any of Formulae (1) to (8), a polymer compound (X) containing a repeating unit represented by Formula (A), and a polymer compound (Y) containing a repeating unit represented by Formula (B) and a repeating unit represented by Formula (C).
• COMPOSITION FOR FORMING GATE INSULATING FILM, ORGANIC THIN FILM TRANSISTOR, ELECTRONIC PAPER, AND DISPLAY DEVICE
  申请人：FUJIFILM Corporation

  公开号：US20160087208A1

  公开（公告）日：2016-03-24

  The present invention provides a composition for forming a gate insulating film, which improves the insulation reliability of an organic thin film transistor without greatly reducing the mobility of the organic thin film transistor, an organic thin film transistor, electronic paper, and a display device. The composition for forming a gate insulating film of the present invention contains an insulating material and a migration inhibitor selected from the group consisting of a compound represented by any of Formulae (1) to (8), a polymer compound (X) containing a repeating unit represented by Formula (A), and a polymer compound (Y) containing a repeating unit represented by Formula (B) and a repeating unit represented by Formula (C).