viridiofungin A | 147023-34-5

• 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: viridiofungin A
• 英文别名: 2-{1-[1-Carboxy-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinic acid；(2S)-2-[(E,2S)-1-[[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-1,11-dioxooctadec-3-en-2-yl]-2-hydroxybutanedioic acid
• CAS: 147023-34-5
• 化学式: C₃₁H₄₅NO₁₀
• 分子量: 591.699
• InChiKey: QSQIZTATOSQHOO-FJOVDUCCSA-N

物化性质

• 沸点：
  854.6±65.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  42
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  199
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  viridiofungin A 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以25%的产率得到2-{1-[1-Carboxy-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-10-oxo-heptadecyl}-2-hydroxy-succinic acid
  参考文献：
  名称：

  REMEDY FOR VIRAL DISEASE

  摘要：

  公开号：

  EP1593378B1
• 作为产物：
  描述：

  (E,2S)-2-[(2S)-2-hydroxy-1,4-bis[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]-11-oxooctadec-3-enoic acid 在 N-甲基吗啉 、 甲酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 viridiofungin A
  参考文献：
  名称：

  Total synthesis of viridiofungin A

  摘要：

  Viridiofungin A，来自绿霉 Trichoderma viride 的一种氨基烷基柠檬酸抗生素，首次以天然存在的形式进行对映体选择性合成，关键步骤是采用手性环氧化物与溴化乙烯镁的区域和立体选择性开环，以及柠檬酸核心与十六烯-15-烯-8-酮的烯烃交叉复分解反应。

  DOI：

  10.1039/b500660k

文献信息

• Total Synthesis of Viridiofungins A and B
  作者：Liselle Atkin、Angus Robertson、Jonathan M. White、Mark A. Rizzacasa

  DOI：10.1021/acs.orglett.1c00971

  日期：2021.5.7

  The total synthesis of viridiofungins A (1) and B (2) via β-lactone 3 in 13 steps is reported. Key steps included an HF-mediated rearrangement of cyclobutene diester 9 to form a bicyclic lactone 6, an olefin cross metathesis between disubstituted alkene 3 and alkene 4 in which isomerization was suppressed, and a novel β-lactone ring opening to form the amide. Deprotection then gave either viridiofungin

  报告了通过13个步骤通过β-内酯3合成viridiofungins A（1）和B（2）的过程。关键步骤包括HF介导的环丁烯二酯9的重排以形成双环内酯6，二取代的烯烃3和烯烃4之间的烯烃交叉复分解（其中异构化被抑制）以及新型的β-内酯开环以形成酰胺。然后脱保护得到高产率的维立芬净A（1）或B（2）。
• Method Of Producing Compound Having Anti-Hcv Activity
  申请人：Aoki Masahiro

  公开号：US20110098477A1

  公开（公告）日：2011-04-28

  There is provided a convenient and inexpensive method of producing a compound which has a high activity of inhibiting replication of hepatitis C virus (HCV) and is useful for preventing and treating a liver disease caused by HCV infection. It is a method of biologically producing a compound represented by the formula (1): [wherein A represents a hydrogen atom, a straight or branched alkyl group having 1 to 8 carbon atoms, or the like], or a pharmaceutically acceptable salt thereof, a method comprising adding an amino acid derivative represented by the formula (3): [wherein A has the same meaning as defined for the compound of the above formula (1); and R represents a hydrogen atom, a straight or branched alkyl group having 1 to 8 carbon atoms, or the like], or a salt thereof into the fungal mycelium or the culture medium/culture broth of a filamentous fungal strain having an ability to produce the compound represented by the formula (2): to thereby cause the fungal strain to directly produce the compound of the formula (1).

  提供了一种方便且廉价的方法，用于生产一种具有高抑制丙型肝炎病毒（HCV）复制活性的化合物，并且可用于预防和治疗由HCV感染引起的肝病。这是一种生物学生产一种由以下化学式（1）表示的化合物的方法：[其中A代表氢原子、具有1至8个碳原子的直链或支链烷基基团，或类似物]，或其药学上可接受的盐的方法，包括将由以下化学式（3）表示的氨基酸衍生物添加到具有生产由以下化学式（2）表示的化合物的能力的丝状真菌菌株的真菌菌丝或培养基/培养液中，从而使真菌菌株直接产生化合物的化学式（1）。
• ORALLY AVAILABLE VIRIDIOFUNGIN DERIVATIVE POSSESSING ANTI-HCV ACTIVITY
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20150210666A1

  公开（公告）日：2015-07-30

  An object of the present invention is to provide a compound that is useful as an orally available anti-HCV agent. The present invention relates to a compound represented by formula (1) or a pharmaceutically acceptable salt thereof. This compound has an anti-HCV activity and is useful as a medicine.

  本发明的目的是提供一种可口服的抗丙型肝炎病毒药物化合物。本发明涉及一种由式（1）所表示的化合物或其药学上可接受的盐。该化合物具有抗丙型肝炎病毒的活性，是一种有用的药物。
• A Stereoselective Synthesis of (−)-Viridiofungin A Utilizing a TiCl₄-Promoted Asymmetric Multicomponent Reaction
  作者：Arun K. Ghosh、Jorden Kass

  DOI：10.1021/ol203093g

  日期：2012.1.20

  A stereoselective synthesis of (-)-viridiofungin A is described. The convergent synthesis utilized a unique highly diastereoselective multicomponent reaction between optically active phenyldihydrofuran and an beta-ketoester to provide two chiral centers including a quarternary carbon center in a single step. Other key steps include an acyloxycarbonium ion-mediated tetrahydrofuran ring-opening reaction and a Julia-Kocienski olefination.
• Production Process of Compound Having Anti-Hcv Action and Intermediate Thereof
  申请人：Kato Tatsuya

  公开号：US20080293950A1

  公开（公告）日：2008-11-27

  A method whereby a compound having HCV replication inhibitory activity and desired optical activity can be synthesized selectively and at high yield in a small number of steps by using a compound having a specific chiral auxiliary as a starting compound is provided. A compound represented by the formula (1-8): [wherein Y represents a group represented by the following formula: Q represents a protected carbonyl group; D represents —(CH 2 ) m —R′, etc.; and n represents an integer of 0 to 10].