methyl 2-tritylamino-4-thiazolylacetate | 78287-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 2-tritylamino-4-thiazolylacetate
• 英文别名: Methyl 2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate；methyl 2-[2-(tritylamino)-1,3-thiazol-4-yl]acetate
• CAS: 78287-71-5
• 化学式: C₂₅H₂₂N₂O₂S
• 分子量: 414.528
• InChiKey: FJQUXGLKXKXXNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  576.4±60.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-tritylamino-4-thiazolylacetate 在 甲醇 、 sodium hydroxide 作用下， 反应 1.0h， 以95%的产率得到<2-(tritylamino)thiazol-4-yl>acetic 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：

  2-氨基噻唑-4-乙酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 methyl 2-tritylamino-4-thiazolylacetate
  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

• 7-(Thiazolylpropionamido) cephalosporins, their preparation, and pharmaceutical compositions containing them
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0021688A1

  公开（公告）日：1981-01-07

  This invention relates to cephalosporin derivatives of the formula wherein R is hydrogen, a lower alkyl group which may have been substituted, or a carbamoyl group which may have been substituted; R, is hydrogen or a methoxy group; R2 is hydrogen, an acyloxy group, or a nitrogen-containing 5-membered heterocyclic thio group which may have been substituted; R3 is a free amino group or an amino group having a protective group; and R. is a free carboxy group or a carboxy group having a protective group; and salts thereof. Such compounds have shown anti-bacterial activity against gram negative bacteria and against gram positive bacteria and may be formulated in a carrier as pharmaceutical compositions. They are made by reacting the corresponding thiazolylpropionic acid derivatives and 7-amino cephalosporin derivatives.

  本发明涉及式中的头孢菌素衍生物 其中 R 是氢、可能已被取代的低级烷基或可能已被取代的氨基甲酰基；R, 是氢或甲氧基；R2 是氢、酰氧基或可能已被取代的含氮五元杂环硫基；R3 是游离氨基或具有保护基的氨基；R. 是游离羧基或具有保护基的羧基；及其盐类。 此类化合物对革兰氏阴性菌和革兰氏阳性菌具有抗菌活性，可作为药物组合物配制在载体中。它们是由相应的噻唑基丙酸衍生物和 7-氨基头孢菌素衍生物反应制成的。
• BETA-LACTAMASE INHIBITORS
  申请人：Protez Pharmaceuticals, Inc.

  公开号：EP2220097A1

  公开（公告）日：2010-08-25
• US4581353A
  申请人：——

  公开号：US4581353A

  公开（公告）日：1986-04-08
• [EN] BETA-LACTAMASE INHIBITORS<br/>[FR] INHIBITEURS DE BÊTA-LACTAMASES
  申请人：PROTEZ PHARMACEUTICALS INC

  公开号：WO2009064414A1

  公开（公告）日：2009-05-22

  Disclosed herein are alpha-aminoboronic acids and their derivatives which act as inhibitors of beta-lactamases. Also disclosed herein are pharmaceutical compositions comprising alpha-aminoboronic acids and methods of use thereof.
• [EN] BETA-LACTAMASE INHIBITORS<br/>[FR] INHIBITEURS DE BÊTA-LACTAMASE
  申请人：PROTEZ PHARMACEUTICALS INC

  公开号：WO2010056827A1

  公开（公告）日：2010-05-20

  Disclosed herein are alpha-aminoboronic acids and their derivatives which act as inhibitors of beta-lactamases. Also disclosed herein are pharmaceutical compositions comprising alpha-aminoboronic acids and methods of use thereof.