(all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid | 178178-39-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid
• 英文别名: Z,Z,Z,Z-(5,8,11,14-Eicosatetraenylthio)-acetic acid；2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenyl]sulfanylacetic acid
• CAS: 178178-39-7
• 化学式: C₂₂H₃₆O₂S
• 分子量: 364.593
• InChiKey: KNLHUNJBRICNPS-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid 在 soybean 15-lipoxygenase 、 potassium phosphate buffer pH 9.0 、 氧气 、 盐酸 、 potassium phosphate buffer 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.92h， 以18%的产率得到(Z,Z,Z,E)-(15-hydroxyeicosa-5,8,11,13-tetraenylthio)acetic acid
  参考文献：
  名称：

  Oxidation of oxa and thia fatty acids and related compounds catalysed by 5- and 15-lipoxygenase

  摘要：

  The modified fatty acids, (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid, 3-[(all-Z)-(eicosa-5,8,11,14-tetraenylthio)]propionic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid, N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine and N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid, all react with soybean 15-lipoxygenase. The products were treated with triphenylphosphine to give alcohols, which were isolated using HPLC. Analysis of the alcohols using negative ion tandem electrospray mass spectrometry, and by comparison with compounds obtained by autoxidation of arachidonic acid, shows that each enzyme catalysed oxidation occurs at the omega -6 position of the substrate. In a similar fashion, it has been found that (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid and N-[(all-Z)-(eicosa-5,8, 11.14-tetraenylthio)]propionic acid each undergoes regioselective oxidation at the carboxyl end of the polyene moiety on treatment with potato 5-lipoxygenase. Neither (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid nor N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid reacts in the presence of this enzyme, while N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine affords the C11' oxidation product. The alcohol derived from (Z,Z,Z)-(octadeca-6,9, 12-trienyloxy)acetic acid using the 15-lipoxygenase reacts at the C6' position with the 5-lipoxygenase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00246-7
• 作为产物：
  描述：

  巯基乙酸 、 arachidonyl bromide 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 16.0h， 以66%的产率得到(all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid
  参考文献：
  名称：

  Synthesis of polyunsaturated β-thia and γ-thia fatty acids from naturally derived polyunsaturated fatty alcohols and in vitro evaluation of their susceptibility to β-oxidation

  摘要：

  A range of polyunsaturated beta- and gamma-thia fatty acids are conveniently prepared in two steps from naturally derived polyunsaturated fatty alcohols. In vitro beta-oxidation studies using acyl Co-A oxidase from Arthrobacter species indicate that (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid, synthesised as reported earlier, (all-Z)-(eicosa-5,8,11,1 4-tetraenylthio)acetic acid and (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid are not susceptible to oxidation, whereas 3-[(all-Z)-(eicosa-5,8, 11,1 4-tetraenylthio)]propionic acid is oxidised with V-o appproximately 40% of that of arachidonic acid. In competitive experiments, none of these novel polyunsaturated fatty acids effect the beta-oxidation of arachidonic acid. (C) 1998 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(98)00002-4

文献信息

• Anti-inflammatory nitro-and thia-fatty acids
  申请人：Ferrante Antonio

  公开号：US20050176815A1

  公开（公告）日：2005-08-11

  The present invention relates to compounds of the general formula: NO 2 -A-B wherein A is a saturated or unsaturated hydrocarbon chain of 14-26 carbon atoms and B is (CH 2 ) n (COOH) m in which n is an integer from 0 to 2 and m is an integer from 0 to 2; or of general formula (I), wherein A′ is a saturated or unsaturated hydrocarbon chain of 9-26 carbon atoms, X is oxygen or is absent and B′ is (CH 2 ) j (COOH) k in which j is an integer from 1 to 3 and k is 0 or 1; and the derivatives thereof in which the hydrocarbon chain includes one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy. These compounds have biological activity, e.g. as anti-infective or anti-inflammatory agents.

  本发明涉及一般式为NO2-A-B的化合物，其中A是14-26个碳原子的饱和或不饱和碳氢链，B是(CH2)n(COOH)min，其中n为0到2的整数，m为0到2的整数；或者一般式(I)中，A'是9-26个碳原子的饱和或不饱和碳氢链，X为氧或不存在，B'为(CH2)j(COOH)kin，其中j为1到3的整数，k为0或1；以及其衍生物，其中碳氢链包括一个或多个羟基、羟过氧基、环氧基和过氧基的取代。这些化合物具有生物活性，例如作为抗感染或抗炎剂。
• Anti-inflammatory nitro- and thia-fatty acids
  申请人：Ferrante Antonio

  公开号：US20050176816A1

  公开（公告）日：2005-08-11

  The present invention relates to compounds of the general formula: NO 2 -A-B wherein A is a saturated or unsaturated hydrocarbon chain of 14-26 carbon atoms and B is (CH 2 ) n (COOH) m in which n is an integer from 0 to 2 and m is an integer from 0 to 2; or of general formula (I), wherein A′ is a saturated or unsaturated hydrocarbon chain of 9-26 carbon atoms, X is oxygen or is absent and B′ is (CH 2 ) j (COOH) k in which j is an integer from 1 to 3 and k is 0 or 1; and the derivatives thereof in which the hydrocarbon chain includes one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy. These compounds have biological activity, e.g. as anti-infective or anti-inflammatory agents.

  本发明涉及一般式为NO2-A-B的化合物，其中A是14-26个碳原子的饱和或不饱和碳氢链，B是（CH2）n（COOH）min，其中n为0到2的整数，m为0到2的整数；或一般式（I）中，A'是9-26个碳原子的饱和或不饱和碳氢链，X是氧或不存在，B'是（CH2）j（COOH）kin，其中j为1到3的整数，k为0或1；以及其中烃链包括一种或多种羟基，羟过氧化物，环氧和过氧化物等取代基的衍生物。这些化合物具有生物活性，例如作为抗感染或抗炎剂。
• Anti-inflammatory nitro- and thia- fatty acids
  申请人：Ferrante Antonio

  公开号：US20050176817A1

  公开（公告）日：2005-08-11

  The present invention relates to compounds of the general formula: NO 2 -A-B wherein A is a saturated or unsaturated hydrocarbon chain of 14-26 carbon atoms and B is (CH 2 ) n (COOH) m in which n is an integer from 0 to 2 and m is an integer from 0 to 2; or of general formula (I), wherein A′ is a saturated or unsaturated hydrocarbon chain of 9-26 carbon atoms, X is oxygen or is absent and B′ is (CH 2 ) j (COOH) k in which j is an integer from 1 to 3 and k is 0 or 1; and the derivatives thereof in which the hydrocarbon chain includes one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy. These compounds have biological activity, e.g. as anti-infective or anti-inflammatory agents.

  本发明涉及一般式为：NO2-A-B的化合物，其中A是14-26个碳原子的饱和或不饱和碳氢链，B是（CH2）n（COOH）min，其中n是0到2的整数，m是0到2的整数；或一般式（I）中，A'是9-26个碳原子的饱和或不饱和碳氢链，X是氧或不存在，B'是（CH2）j（COOH）kin，其中j是1到3的整数，k是0或1；以及其衍生物，其中碳氢链包括羟基，过氧化氢基，环氧基和过氧基中的一种或多种取代物。这些化合物具有生物活性，例如作为抗感染或抗炎剂。
• Anti-cancer nitro- and thia-fatty acids
  申请人：Ferrante Antonio

  公开号：US20050222253A1

  公开（公告）日：2005-10-06

  The present invention relates to pharmaceutical compositions comprising, as an anticancer agent: (a) one or more compounds having the formula NO 2 -A-B, wherein A is a saturated or unsaturated hydrocarbon chain of 14-26 double bonds, and B is (CH 2 ) m (COOH) n in which n is an integer from 0 to 2 and m is an integer from 0 to 2; or a derivative thereof in which the hydrocarbon chain has one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy; (b) one or more compounds selected from polyunsaturated fatty acids (PUFA's) having a 16 to 26 carbon atom chain and 3 to 6 double bonds, and wherein the PUFA is covalently coupled at the carboxylic acid group to an amino acid selected from glycine and aspartic acid; (c) one or more compounds selected from unsaturated fatty acids having an 18 to 25 carbon atom chain and 1 to 6 double bonds and wherein the fatty acid has one or two β-oxa, γ-oxa, β-thia, γ-thia substitutions; or (d) one or more compounds having formula (I) wherein A′ is a saturated or unsaturated hydrocarbon chain of 9-26 carbon atoms, X is oxygen or is absent and B′ is (CH 2 ) j (COOH) k in which j is an integer from 1 to 3 and k is 0 or 1; or a derivative thereof in which the hydrocarbon chain has one or more than one substitution selected from the group consisting of hydroxy, hydroperoxy, epoxy and peroxy; and a pharmaceutically acceptable carrier or diluent.

  本发明涉及制药组合物，包括以下抗癌剂：(a) 一个或多个具有NO2-A-B公式的化合物，其中A是14-26个双键的饱和或不饱和碳氢链，B是(CH2)m(COOH)，其中n是0到2的整数，m是0到2的整数；或者其衍生物，其中碳氢链具有羟基，羟过氧化物，环氧和过氧化物中的一个或多个取代物；(b) 一个或多个选择自具有16到26个碳原子链和3到6个双键的多不饱和脂肪酸（PUFA），其中PUFA在羧酸基上与甘氨酸和天冬氨酸中选择的一种氨基酸共价耦合；(c) 一个或多个选择自具有18到25个碳原子链和1到6个双键的不饱和脂肪酸，其中脂肪酸具有一个或两个β-氧杂，γ-氧杂，β-硫杂，γ-硫杂取代物；或(d) 一个或多个具有公式(I)的化合物，其中A'是9-26个碳原子的饱和或不饱和碳氢链，X是氧或不存在，B'是(CH2)j(COOH)，其中j是1到3的整数，k是0或1；或者其衍生物，其中碳氢链具有羟基，羟过氧化物，环氧和过氧化物中的一个或多个取代物；以及药学上可接受的载体或稀释剂。
• EP0869941A4
  申请人：——

  公开号：EP0869941A4

  公开（公告）日：1998-10-14