(3R,4S)-四氢-3,4-呋喃二甲酸 | 149429-49-2

• 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
• 中文名称: (3R,4S)-四氢-3,4-呋喃二甲酸
• 英文名称: (3R,4S)-tetrahydrofuran-3,4-dicarboxylic acid
• 英文别名: cis-tetrahydrofuran-3,4-dicarboxylic acid；cis-Tetrahydro-furan-3,4-dicarboxylic acid；(3S,4R)-oxolane-3,4-dicarboxylic acid
• CAS: 149429-49-2
• 化学式: C₆H₈O₅
• 分子量: 160.127
• InChiKey: QUHAOMPZQHGTKN-ZXZARUISSA-N

物化性质

• 沸点：
  425.5±45.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-四氢-3,4-呋喃二甲酸 在 乙酸酐 作用下， 反应 18.0h， 生成 (3a,6a-cis)-tetrahydrofuro[3,4-c]furan-1,3-dione
  参考文献：
  名称：

  [EN] NOVEL HEPATITIS C VIRUS INHIBITORS
  [FR] NOUVEAUX INHIBITEURS DU VIRUS DE L'HÉPATITE C

  摘要：

  本发明提供了式(I)的化合物：其中环A和A'独立地是5个成员的可选取代的芳香杂环；Q是C(=O)NR1R1'或式U是C(R4)2，O，S，S(=O)2，C(R4)2C(R4)2，CH2O，OCH2，CH2S，SCH2，CH2S(=O)2，S(=O)CH2或C=C(Ru)2；X是CH2，CHR12，CR12R12，O，S，S(=O)2或NRx；m是0，1，2或3；n是0，1，2或3；其他变量如权利要求中所定义，用于治疗或预防丙型肝炎病毒感染，以及相关方面。

  公开号：

  WO2013095275A1
• 作为产物：
  描述：

  3,4-呋喃二甲酸 在 5% rhodium on alumina 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、620.54 kPa 条件下， 反应 4.0h， 生成 (3R,4S)-四氢-3,4-呋喃二甲酸 、 trans-tetrahydrofuran-3,4-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge

  摘要：

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.004

文献信息

• [EN] NOVEL HEPATITIS C VIRUS INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：MEDIVIR AB

  公开号：WO2013095275A1

  公开（公告）日：2013-06-27

  The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

  本发明提供了式(I)的化合物：其中环A和A'独立地是5个成员的可选取代的芳香杂环；Q是C(=O)NR1R1'或式U是C(R4)2，O，S，S(=O)2，C(R4)2C(R4)2，CH2O，OCH2，CH2S，SCH2，CH2S(=O)2，S(=O)CH2或C=C(Ru)2；X是CH2，CHR12，CR12R12，O，S，S(=O)2或NRx；m是0，1，2或3；n是0，1，2或3；其他变量如权利要求中所定义，用于治疗或预防丙型肝炎病毒感染，以及相关方面。
• 3-(5-HYDROXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF
  申请人：Novartis AG

  公开号：US20200017461A1

  公开（公告）日：2020-01-16

  The present disclosure provides a compound of Formula (I′): or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof, wherein R x , X 1 , X 2 , and R 1 are as defined herein, and methods of making and using same.

  本公开提供了化合物Formula (I′)的一种： 或其药用可接受的盐、水合物、溶剂合物、前药、立体异构体或互变异构体，其中R x 、X 1 、X 2 和R 1 如本文所定义，并提供了制备和使用该化合物的方法。
• [EN] FUNGICIDES<br/>[FR] FONGICIDES
  申请人：ZENECA LIMITED

  公开号：WO1995007022A1

  公开（公告）日：1995-03-16

  (EN) A method of combating fungi which comprises applying to a plant, to a seed of a plant or to the locus of a seed or plant a compound of formula (I), wherein X is O, S, SO, SO2, NR8 or CLM; A, B, D, E, L and M are, independently, hydrogen, halogen, alkyl, mono- or di-haloalkyl, benzyl (optionally substituted by halogen or haloalkyl) or hydroxy; A and B or D and E or L and M may together form a =S, =O or =CR6R7 group; B and L or D and L may together form a bond; V is O or NR4; R1 and R2 are, independently, hydrogen or an amine protecting group; R3, R4 and R8 are, independently, hydrogen, alkyl or benzyl; R6 and R7 are, independently, hydrogen, halogen, alkyl, phenyl, benzyl, alkoxy or acyloxy; or a salt thereof; provided that when X is CLM, R1, R2, R3, A, M, D and E are all hydrogen, L and B are either both hydrogen or together form a bond, and V is O then the compound of formula (I) is in the form of a salt, but not a hydrochloride salt.(FR) L'invention concerne un procédé de lutte contre les champignons, qui comprend l'application sur une plante, sur une graine d'une plante ou sur le site de la graine ou de la plante, d'un composé de formule (I), dans laquelle X représente O, S, SO, SO2, NR8 ou CLM; A, B, D, E, L et M représentent indépendamment hydrogène, halogène, alkyle, mono- ou di-haloalkyle, benzyle (facultativement substitué par halogène ou haloalkyle) ou hydroxy; A et B ou D et E ou L et M peuvent former ensemble un groupe =S, =O ou =CR6R7; B et L ou D et L peuvent former ensemble une liaison; V représente O ou NR4; R1 et R2 représentent indépendamment hydrogène ou un groupe protecteur d'amines; R3, R4 et R8 représentent indépendamment hydrogène, alkyle ou benzyle; R6 et R7 représentent indépendamment hydrogène, halogène, alkyle, phényle, benzyle, alcoxy or acyloxy; ou un de leurs sels; à condition que lorsque X représente CLM, R1, R2, R3, A, M, D et E représentent tous hydrogène, L et B soit représentent tous deux hydrogène soit forment ensemble une liaison, et V représente O, alors, le composé de la formule (I) est sous la forme d'un sel qui n'est pas un sel de chlorhydrate.
• Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
  作者：Ali Thaqi、Janet L. Scott、Jayne Gilbert、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.ejmech.2010.01.004

  日期：2010.5

  Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Delta-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin. anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.