methyl 2'-(2-bromo-1,1-dimethoxyethyl)-5-phenyl-[2,4']bis-oxazolyl-4-carboxylate | 930285-04-4

• 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 2'-(2-bromo-1,1-dimethoxyethyl)-5-phenyl-[2,4']bis-oxazolyl-4-carboxylate
• 英文别名: Methyl 2-[2-(2-bromo-1,1-dimethoxyethyl)-1,3-oxazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxylate
• CAS: 930285-04-4
• 化学式: C₁₈H₁₇BrN₂O₆
• 分子量: 437.247
• InChiKey: LISDIVVSUPTCBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2'-(2-bromo-1,1-dimethoxyethyl)-5-phenyl-[2,4']bis-oxazolyl-4-carboxylate 在 lithium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Synthesis of IB-01211, a Cyclic Peptide Containing 2,4-Concatenated Thia- and Oxazoles, via Hantzsch Macrocyclization

  摘要：

  An efficient and versatile convergent synthesis of IB-01211 based on a combination of peptide and heterocyclic chemistry is described. The key step in the synthesis is macrocyclization through intramolecular Hantzsch formation of the thiazole ring. Dehydration of a free primary alcohol to furnish the exocyclic methylidene present in the natural product was applied during the macrocyclization.

  DOI：

  10.1021/ol063023c
• 作为产物：
  描述：

  D,L-phenylserine methyl ester hydrochloride 在 二乙胺基三氟化硫 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 146.16h， 生成 methyl 2'-(2-bromo-1,1-dimethoxyethyl)-5-phenyl-[2,4']bis-oxazolyl-4-carboxylate
  参考文献：
  名称：

  Synthesis of IB-01211, a Cyclic Peptide Containing 2,4-Concatenated Thia- and Oxazoles, via Hantzsch Macrocyclization

  摘要：

  An efficient and versatile convergent synthesis of IB-01211 based on a combination of peptide and heterocyclic chemistry is described. The key step in the synthesis is macrocyclization through intramolecular Hantzsch formation of the thiazole ring. Dehydration of a free primary alcohol to furnish the exocyclic methylidene present in the natural product was applied during the macrocyclization.

  DOI：

  10.1021/ol063023c

文献信息

• Preparation of penta-azole containing cyclopeptides: challenges in macrocyclization
  作者：Delia Hernández、Estela Riego、Andrés Francesch、Carmen Cuevas、Fernando Albericio、Mercedes Álvarez

  DOI：10.1016/j.tet.2007.06.103

  日期：2007.9

  Herein is described the synthesis of several analogs of the natural product IB-01211 from concatenated azoles, via a biomimetic pathway based on cyclization-oxidation of serine containing peptides combined with the Hantzsch synthesis. The macrocyclization of rigid peptide compounds 1 and 2 to give IB-01211 and its epimer 12b was explored, and the results are compared here to those previously obtained for the macrocyclization of more flexible structures in the syntheses of YM-216391, telomestatin, and IB-01211. Lastly, the preliminary results of anti-tumor activity screening of the synthesized analogs are discussed. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and Antitumor Activity of Mechercharmycin A Analogues
  作者：Delia Hernández、Marta Altuna、Carmen Cuevas、Rosa Aligué、Fernando Albericio、Mercedes Álvarez

  DOI：10.1021/jm800513w

  日期：2008.9.25

  Several analogues of the cytotoxic thiopeptide IB-01211 or mechercharmycin A (1) have been synthesized. The cytotoxicity of 1 and the synthesized analogues were evaluated against a panel of three human tumor cell lines. Thiopeptide 1 and the most active derivatives 2 and 3c were chosen for further studies on effects on cell cycle progression and induction of apoptosis. Interestingly, the inhibition of cell division and activation of a programmed cell death by apoptosis were detected.
• Synthesis of IB-01211, a Cyclic Peptide Containing 2,4-Concatenated Thia- and Oxazoles, via Hantzsch Macrocyclization
  作者：Delia Hernández、Gemma Vilar、Estela Riego、Librada M. Cañedo、Carmen Cuevas、Fernando Albericio、Mercedes Álvarez

  DOI：10.1021/ol063023c

  日期：2007.3.1

  An efficient and versatile convergent synthesis of IB-01211 based on a combination of peptide and heterocyclic chemistry is described. The key step in the synthesis is macrocyclization through intramolecular Hantzsch formation of the thiazole ring. Dehydration of a free primary alcohol to furnish the exocyclic methylidene present in the natural product was applied during the macrocyclization.