2-苯甲酰氨基-3-(4-(苯甲酰氧基)苯基)丙酸 | 97485-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 2-苯甲酰氨基-3-(4-(苯甲酰氧基)苯基)丙酸
• 英文名称: 2-benzamido-3-(4-(benzoyloxy)phenyl)propanoic acid
• 英文别名: O,N-dibenzoyltyrosine；N,O-dibenzoyl-DL-tyrosine；N,O-Dibenzoyl-DL-tyrosin；N,O-Dibenzoyl-tyrosin；2-(Benzoylamino)-3-(4-benzoyloxyphenyl)propionic acid；2-benzamido-3-(4-benzoyloxyphenyl)propanoic acid
• CAS: 97485-13-7
• 化学式: C₂₃H₁₉NO₅
• 分子量: 389.408
• InChiKey: UMTSYXVWHRVSQY-UHFFFAOYSA-N

物化性质

• 沸点：
  657.7±55.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-苯甲酰氨基-3-(4-(苯甲酰氧基)苯基)丙酸 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 2-苯甲酰氨基-3-(4-羟基苯基)丙酸
  参考文献：
  名称：

  Synthesis and Protein Kinase C Inhibitory Activities of Acyclic Balanol Analogs That Are Highly Selective for Protein Kinase C over Protein Kinase A

  摘要：

  A series of balanol analogs in which the perhydroazepine ring and the p-hydroxybenzamide moiety were combined into an acyclic linked unit have been prepared and evaluated for their inhibitory properties against the serine/threonine kinase PKC. Several low-micromolar to low-nanomolar inhibitors of the alpha, beta(I), beta(II), gamma, delta, epsilon, and eta PKC: isozymes were prepared. In general, these acyclic balanol analogs were found to be highly selective for PKC over the serine/threonine kinase PKA. The type and number of atoms linking the benzophenone ester to the p-hydroxyphenyl group necessary for optimal PKC inhibition were investigated. The most potent compounds contained a three-carbon linker in which the carboxamide moiety of balanol had been replaced by a methylene group. The effect of placing substituents on the three-carbon chain was also investigated. The preferred compounds contained either a 2-benzenesulfonamido (6b) or a 1-methyl (21b) substituent. The preferred compounds 6b and 21b were tested against a panel of serine/threonine kinases and found to be highly selective for PKC. The more active enantiomer of 6b, (S)-12b, was 3-10-fold more active than the R-enantiomer against the PKC isozymes. The effect of making the analogs more rigid by making the three-carbon chain part of a five-membered ring, but with retention of the methylene replacement for the carboxamide moiety, led to potent PKC inhibitors including anti-substituted pyrrolidine analog 35b and the most potent PKC inhibitor in the series, anti-substituted cyclopentane analog 29b. The anti cyclopentane analog 29b was a low-micromolar inhibitor of the PMA-induced superoxide burst in neutrophils, and its carboxylic ester was a high-nanomolar inhibitor of neutrophils. Finally esterification of 21b, (S)-12b, and 35b turned these potent PKC inhibitors into low-micromolar inhibitors of neutrophils.

  DOI：

  10.1021/jm960581w
• 作为产物：
  描述：

  4-benzoyloxy-L-phenylalanine 以93的产率得到2-苯甲酰氨基-3-(4-(苯甲酰氧基)苯基)丙酸
  参考文献：
  名称：

  一种苯丙氨醇化合物的光学异构体的制备方法 及其用途

  摘要：

  本发明公开了N-[N-苯甲酰基-O-(2-二甲氨基乙基)-L-酪氨酰基]-L-苯丙氨醇的光学异构体的制备方法及其用途，以L-酪氨酸或D-酪氨酸为起始原料，经过酰化、缩合、水解和烷基化反应得到产物。与现有技术相比，本发明采用优化的合成路线和反应条件，所用反应原料和试剂价廉、易得，整个合成反应的条件比较温和，可控性强，操作简单；与专利2006102010164相比，本发明合成的产物收率由10%提高到30%，产物纯度由92%提高至99%；该合成工艺的重复性好，有利于进行工业化大生产。另外，生物活性研究表明：本发明制得的其中两个光学异构体对HBV？DNA有明显的抑制作用，可将其用于制备抗HBV感染的药物。

  公开号：

  CN103508920B

文献信息

• [EN] ANTIBACTERIAL AGENTS: N(ALPHA)-AROYL-N-ARYL-PHENYLALANINAMIDES<br/>[FR] AGENTS ANTIBACTÉRIENS : N (ALPHA)-AROYL-N-ARYL-PHÉNYLALANINAMIDES
  申请人：UNIV RUTGERS

  公开号：WO2015120320A1

  公开（公告）日：2015-08-13

  The invention provides compounds having activity as bacterial RNA polymerase inhibitors and antibacterial agents, as well as compositions comprising the compounds and methods for their use. Specifically, phenylalanineamide and tyrosinamide compounds are disclosed that have inhibitory activity toward mycobacterium tuberculosis RNA polymerase. Use of these compounds in the treatment o prevention of M. tuberculosis infections in a mammal, is disclosed.

  该发明提供了具有细菌RNA聚合酶抑制剂和抗菌剂活性的化合物，以及包含这些化合物的组合物和它们的使用方法。具体地，揭示了对结核分枝杆菌RNA聚合酶具有抑制活性的苯丙氨酰胺和酪氨酰胺化合物。还揭示了在哺乳动物中使用这些化合物治疗或预防结核分枝杆菌感染的方法。
• .alpha.-allenic-.alpha.-amino acids as enzyme inhibitors
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04661510A1

  公开（公告）日：1987-04-28

  Novel .alpha.-allenic-.alpha.-amino acids which are enzyme inhibitors of the suicide or k.sub.cat type are disclosed herein.

  本文披露了一种新型的α-异戊烯-α-氨基酸，它们是自杀酶抑制剂或k.sub.cat型酶抑制剂。
• Alpha-allenic-alpha-amino acids
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0134561A1

  公开（公告）日：1985-03-20

  Novel alpha-allenic-alpha-amino acids which are enzyme inhibitors of the suicide or kcat type are disclosed herein.

  本文公开了作为自杀或 kcat 型酶抑制剂的新型α-烯-α-氨基酸。
• 一种盐酸替罗酰胺的生产工艺
  申请人：苏州诚和医药化学有限公司

  公开号：CN114989033A

  公开（公告）日：2022-09-02

  本申请涉及有机合成的技术领域，具体公开了一种盐酸替罗酰胺的生产工艺，包括以下步骤：利用络氨酸、苯甲酰氯制得O,N‑二苯甲酰‑酪氨酸；利用O,N‑二苯甲酰‑酪氨酸、二正丙胺制得N‑苯甲酰基‑酪氨酰二正丙胺，利用碾压装置对N‑苯甲酰基‑酪氨酰二正丙胺进行碾压；在复合催化剂的作用下，利用N‑苯甲酰基‑酪氨酰二正丙胺、2‑二乙氨基氯乙烷盐酸盐制得产品盐酸替罗酰胺。本申请中先利用碾压装置对N‑苯甲酰基‑酪氨酰二正丙胺进行碾压，再利用复合催化剂进行催化，提高了制得盐酸替罗酰胺的纯度。
• Suda, Kohji; Hino, Fumio; Yijima, Chino, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 2, p. 882 - 885
  作者：Suda, Kohji、Hino, Fumio、Yijima, Chino

  DOI：——

  日期：——