(+)-epopromycin B

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-epopromycin B
• 英文别名: Epopromycin B；N-[(2S)-3-hydroxy-1-[[(2S)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]-7-methyloctanamide
• 化学式: C₂₁H₃₈N₂O₆
• 分子量: 414.543
• InChiKey: DXOXZURUMIOSAK-XGHQBKJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-溴戊酸甲酯 在 palladium on activated charcoal 咪唑 、 lithium hydroxide 、 N-羟基丁二酰亚胺 、 氢氟酸 、 氢气 、 sodium hydride 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.0h， 生成 (+)-epopromycin B
  参考文献：
  名称：

  Total synthesis of (+)-epopromycin B and its analogues—studies on the inhibition of cellulose biosynthesis

  摘要：

  The described inhibition of the cellulose biosynthesis by epopromycin B prompted us to establish a short and efficient synthesis of the natural product, suitable for accessing a broad range of unnatural analogues in a multiparallel fashion. During the course of our synthesis the absolute configuration of (+)-epopromycin B could be determined. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01944-4

文献信息

• COMPOSITIONS AND METHODS FOR INHIBITING PROTEASES
  申请人：Gerwick William H.

  公开号：US20140248333A1

  公开（公告）日：2014-09-04

  In particular, in alternative embodiments, the invention provides pharmaceutical compounds and formulations comprising a family of epoxyketone compounds, which include racemic mixtures or racemates, isomers, stereoisomers, diastereoisomers, derivatives and analogs, and methods for making and using them. In alternative embodiments, pharmaceutical compositions and formulations of the invention are administered to an individual in need thereof in an amount sufficient to treat, prevent, reverse and/or ameliorate an infection, disease or condition that can be ameliorated, treated, prevented or reversed by partially or completely inhibiting a chymotrypsin-like protease or a proteasome activity, including e.g., a retroviral infection such as human immunodeficiency virus-1 (HIV-1) infection, an immune disorder, a neurodegenerative disease or condition, or a cancer such as a myeloma or multiple myeloma, an adenocarcinoma such as a lung adenocarcinoma, a pancreatic cancer, a B-cell related cancer, and lymphomas such as non-Hodgkin's lymphoma.
• US9409944B2
  申请人：——

  公开号：US9409944B2

  公开（公告）日：2016-08-09
• Total synthesis of (+)-epopromycin B and its analogues—studies on the inhibition of cellulose biosynthesis
  作者：Markus R Dobler

  DOI：10.1016/s0040-4039(00)01944-4

  日期：2001.1

  The described inhibition of the cellulose biosynthesis by epopromycin B prompted us to establish a short and efficient synthesis of the natural product, suitable for accessing a broad range of unnatural analogues in a multiparallel fashion. During the course of our synthesis the absolute configuration of (+)-epopromycin B could be determined. (C) 2000 Elsevier Science Ltd. All rights reserved.