2-benzyloxyimino-3-(3,5-dibromo-4-hydroxyphenyl)propionic acid | 740808-92-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-benzyloxyimino-3-(3,5-dibromo-4-hydroxyphenyl)propionic acid
• 英文别名: 3-(3,5-dibromo-4-hydroxyphenyl)-2-phenylmethoxyiminopropanoic acid
• CAS: 740808-92-8
• 化学式: C₁₆H₁₃Br₂NO₄
• 分子量: 443.092
• InChiKey: BAANKIZXIABBIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.12
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-benzyloxyimino-3-(3,5-dibromo-4-hydroxyphenyl)propionic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis of a bromotyrosine-derived natural product inhibitor of mycothiol- S -conjugate amidase

  摘要：

  Recently we described the structures of two new bromotyrosine-derived alkaloids that inhibit the detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis. Here we describe a concise total synthesis of bromotyrosine oxime 1. The six-step synthesis of 1 utilized a trifluoromethyloxazole intermediate, whose hydrolysis product underwent alkylation and coupling to agmatine to give the inhibitor in similar to40% overall yield. Oxime 1 inhibited MCA and its homolog AcGI deacetylase with IC50 values of 30 and 150 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.095
• 作为产物：
  描述：

  Trifluoro-acetic acid 2,6-dibromo-4-(5-oxo-2-trifluoromethyl-4,5-dihydro-oxazol-4-ylmethyl)-phenyl ester 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 2-benzyloxyimino-3-(3,5-dibromo-4-hydroxyphenyl)propionic acid
  参考文献：
  名称：

  Synthesis of a bromotyrosine-derived natural product inhibitor of mycothiol- S -conjugate amidase

  摘要：

  Recently we described the structures of two new bromotyrosine-derived alkaloids that inhibit the detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis. Here we describe a concise total synthesis of bromotyrosine oxime 1. The six-step synthesis of 1 utilized a trifluoromethyloxazole intermediate, whose hydrolysis product underwent alkylation and coupling to agmatine to give the inhibitor in similar to40% overall yield. Oxime 1 inhibited MCA and its homolog AcGI deacetylase with IC50 values of 30 and 150 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.095

文献信息

• Structure-Activity Relationships Study of Bastadin 6, an Anti-Angiogenic Brominated-Tyrosine Derived Metabolite from Marine Sponge
  作者：Naoyuki Kotoku、Atsushi Hiramatsu、Hiroaki Tsujita、Yoichi Hirakawa、Mami Sanagawa、Shunji Aoki、Motomasa Kobayashi

  DOI：10.1002/ardp.200700231

  日期：2008.9

  A structure‐activity relationship (SAR) study of bastadin 6 (1), a brominated tyrosine‐derived metabolite from Indonesian marine sponge having a potent anti‐angiogenic activity, was executed. The syntheses and their biological evaluation of the oxime‐modified analogues and bromine‐modified analogues revealed that both the oxime moieties and bromine atoms in bastadin 6 (1) play an important role to

  对 bastadin 6 (1) 进行了构效关系 (SAR) 研究，bastadin 6 (1) 是一种来自印度尼西亚海绵的溴化酪氨酸衍生代谢物，具有强大的抗血管生成活性。肟修饰类似物和溴修饰类似物的合成及其生物学评价表明，bastadin 6 (1) 中的肟部分和溴原子都发挥重要作用，显示出对人脐静脉的有效和选择性抗增殖活性内皮细胞 (HUVEC)。
• Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge
  作者：Naoyuki Kotoku、Hiroaki Tsujita、Atsushi Hiramatsu、Chinatsu Mori、Noriko Koizumi、Motomasa Kobayashi

  DOI：10.1016/j.tet.2005.05.038

  日期：2005.7

  An efficient total synthesis of bastadin 6 (1), a cyclic tetramer of brominated tyrosine derivatives from the marine sponge, Ianthella basta, with selective anti-angiogenic activity, was accomplished. We developed a novel Ce(IV)-mediated oxidative coupling reaction of 2,6-dibromophenols to give the diaryl ether derivatives, the characteristic segment of 1. Condensation of two segments and subsequent

  有效地全合成了bastadin 6（1），这是一种来自海洋海绵Ianthella basta的溴化酪氨酸衍生物的环状四聚体，具有选择性的抗血管生成活性。我们开发了一种新型的Ce（IV）介导的2,6-二溴苯酚的氧化偶联反应，得到特征部分为1的二芳基醚衍生物。两个片段的缩合和随后的分子内大环化在九个步骤中得到了basastin 6（1），总产率为26％。