linolenyl hydrazide | 1169394-01-7

• 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: linolenyl hydrazide
• 英文别名: Linolenic acid hydrazide；(9Z,12Z,15Z)-octadeca-9,12,15-trienehydrazide
• CAS: 1169394-01-7
• 化学式: C₁₈H₃₂N₂O
• 分子量: 292.465
• InChiKey: FGTSIDZFACFJDS-PDBXOOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  阿霉素 、 linolenyl hydrazide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以49.4%的产率得到(9Z,12Z,15Z)-N'-(1-((2S,4S)-4-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)-2-hydroxyethylidene)octadeca-9,12,15-trienehydrazide
  参考文献：
  名称：

  Synthesis of Doxorubicin α-Linolenic Acid Conjugate and Evaluation of Its Antitumor Activity

  摘要：

  Doxorubicin (DOX) is a broad-spectrum antitumor drug used in the clinic. However, it can cause serious heart toxicity. To increase the therapeutic index of DOX and to attenuate its toxicity toward normal tissues, we conjugated DOX with either alpha-linolenic acid (LNA) or palmitic acid (PA) by a hydrazone or an amide bond to produce DOX-hyd-LNA, DOX-ami-LNA, DOX-hyd-PA, and DOX-ami-PA. The cytotoxicity of DOX-hyd-LNA on HepG2, MCF-7, and MDA-231 cells was higher compared to that of DOX, DOX-ami-LNA, DOX-hyd-PA, and DOX-ami-PA. The cytotoxicity of DOX-hyd-LNA on HUVECs was lower than that of DOX. DOX-hyd-LNA released significantly more DOX in pH 5.0 medium than it did in pH 7.4 medium. DOX-hyd-LNA induced more apoptosis in MCF-7 and HepG2 cells than DOX or DOX-ami-LNA. Significantly more DOX was released from DOX-hyd-LNA in both MCF-7 and HepG2 cells compared with DOX-ami-LNA. Compared to free DOX, a biodistribution study showed that DOX-hyd-LNA greatly increased the content of DOX in tumor tissue and decreased the content of DOX in heart tissue after it was intravenously administered. DOX-hyd-LNA improved the survival rate, prolonged the life span, and slowed the growth of the tumor in tumor-bearing nude mice. These results indicate that DOX-hyd-LNA improved the therapeutic index of DOX. Therefore, DOX-hyd-LNA is a potential compound for use as a cancer-targeting therapy.

  DOI：

  10.1021/mp4004139
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 linolenyl hydrazide
  参考文献：
  名称：

  Synthesis of Doxorubicin α-Linolenic Acid Conjugate and Evaluation of Its Antitumor Activity

  摘要：

  Doxorubicin (DOX) is a broad-spectrum antitumor drug used in the clinic. However, it can cause serious heart toxicity. To increase the therapeutic index of DOX and to attenuate its toxicity toward normal tissues, we conjugated DOX with either alpha-linolenic acid (LNA) or palmitic acid (PA) by a hydrazone or an amide bond to produce DOX-hyd-LNA, DOX-ami-LNA, DOX-hyd-PA, and DOX-ami-PA. The cytotoxicity of DOX-hyd-LNA on HepG2, MCF-7, and MDA-231 cells was higher compared to that of DOX, DOX-ami-LNA, DOX-hyd-PA, and DOX-ami-PA. The cytotoxicity of DOX-hyd-LNA on HUVECs was lower than that of DOX. DOX-hyd-LNA released significantly more DOX in pH 5.0 medium than it did in pH 7.4 medium. DOX-hyd-LNA induced more apoptosis in MCF-7 and HepG2 cells than DOX or DOX-ami-LNA. Significantly more DOX was released from DOX-hyd-LNA in both MCF-7 and HepG2 cells compared with DOX-ami-LNA. Compared to free DOX, a biodistribution study showed that DOX-hyd-LNA greatly increased the content of DOX in tumor tissue and decreased the content of DOX in heart tissue after it was intravenously administered. DOX-hyd-LNA improved the survival rate, prolonged the life span, and slowed the growth of the tumor in tumor-bearing nude mice. These results indicate that DOX-hyd-LNA improved the therapeutic index of DOX. Therefore, DOX-hyd-LNA is a potential compound for use as a cancer-targeting therapy.

  DOI：

  10.1021/mp4004139

文献信息

• Synthesis, Evaluation and Molecular Docking Studies of 1,3,4-oxadiazole- 2-thiol Incorporating Fatty Acid Moiety as Antitumor and Antimicrobial Agents
  作者：Fatma Mohamed、Ahmed Hashem、Randa Swellem、Galal Nawwar

  DOI：10.2174/157018081131000072

  日期：2014.2

  A series of 1,3,4-oxadiazole-2-thiol incorporating fatty acid moieties was synthesized. The chemical structure of the synthesized compounds was established by their spectral data, elemental analysis, and their chemical behavior. Their thioglycosides derivatives and the analogous 1,2,4-triazole were also prepared. The in vitro cytotoxicty of the synthesized compounds was screened against two cell lines; breast cell line MCF-7, and liver cell line HepG2. The most potent compound is (E)-5-(heptadec-8-enyl)-1,3,4-oxadiazole-2-thiol 4f with IC50 (2.82 | µg/ml) and (3.87 µg/ml) against breast cell line MCF-7 and liver cell line HepG2 respectively. Molecular Docking study of Bcl-2 was conducted for the most potent compound, its analogues and the lowest cytotoxicty compound. The antimicrobial activity was also screened, compound (E)-5-ethyl-1,3,4-oxadiazole-2-thiol 4a showed a broad spectrum of activity. A relationship between the length of the fatty acid chain and the biological activity was noticed in the tested compounds.

  一系列含有脂肪酸基团的1,3,4-噁二唑-2-硫醇化合物被合成。通过光谱数据、元素分析和化学行为确定了合成分子的化学结构。它们的硫代糖苷衍生物及其类似的1,2,4-三唑化合物也被制备。体外细胞毒性测试对两种细胞系进行了筛选：乳腺癌细胞系MCF-7和肝癌细胞系HepG2。最具活性的化合物是(E)-5-(十七碳-8-烯基)-1,3,4-噁二唑-2-硫醇4f，其对MCF-7细胞系的IC50值为2.82 µg/ml，对HepG2细胞系的IC50值为3.87 µg/ml。对最具活性化合物、其类似物和最低细胞毒性化合物的Bcl-2分子对接研究进行了开展。抗微生物活性也被筛选，化合物(E)-5-乙基-1,3,4-噁二唑-2-硫醇4a显示出广谱活性。在测试的化合物中，注意到脂肪酸链的长度与生物活性之间存在关系。
• POLYACETAL RESIN COMPOSITION
  申请人：Polyplastics Co., Ltd.

  公开号：EP1674526A1

  公开（公告）日：2006-06-28

  A polyacetal resin composition comprises a polyacetal resin, and at least one carboxylic acid hydrazide selected from a saturated or unsaturated long-chain aliphatic carboxylic acid hydrazide, a saturated or unsaturated alicyclic carboxylic acid hydrazide, a dimer acid or trimer acid hydrazide, and an oxycarboxylic acid hydrazide corresponding to each of these hydrazides. The proportion of the carboxylic acid hydrazide may be about 0.001 to 20 parts by weight relative to 100 parts by weight of the polyacetal resin. The polyacetal resin composition may further comprise at least one member selected from an antioxidant, a heat stabilizer, a processing stabilizer, a weather (light)-resistant stabilizer, an impact resistance improver, a slip-improving agent, a coloring agent, and a filler. With the use of such a resin composition, stability of a polyacetal resin is improved, and formaldehyde emission is inhibited.

  聚缩醛树脂组合物由聚缩醛树脂和至少一种羧酸酰肼组成，羧酸酰肼选自饱和或不饱和长链脂族羧酸酰肼、饱和或不饱和脂环族羧酸酰肼、二聚酸或三聚酸酰肼以及与上述每种酰肼相对应的氧羧酸酰肼。相对于 100 重量份的聚缩醛树脂，羧酸酰肼的比例可以是约 0.001 至 20 重量份。聚缩醛树脂组合物还可以包含至少一种选自抗氧化剂、热稳定剂、加工稳定剂、耐候（光）稳定剂、抗冲击性改进剂、滑爽性改进剂、着色剂和填料的成分。使用这种树脂组合物可以提高聚缩醛树脂的稳定性，并抑制甲醛释放。
• Modulation of doxorubicin activity in cancer cells by conjugation with fatty acyl and terpenyl hydrazones
  作者：K. Effenberger、S. Breyer、R. Schobert

  DOI：10.1016/j.ejmech.2010.01.037

  日期：2010.5

  Doxorubicin N-acylhydrazones derived from saturated, unsaturated and terpene-terminated fatty acids were tested for anticancer activity in cells of human HL-60 leukaemia, 518A2 melanoma, MCF-7/Topo breast and KB-V1/Vbl cervix carcinomas. In the latter, the N-heptadecanoyl hydrazone was more cytotoxic than its unsaturated C(18)-fatty acyl analogues and even three times more than doxorubicin. The (menthoxycarbonyl)undecanoyl hydrazone was twice as active as doxorubicin in these multidrug resistant KB-V1/Vbl and in the 518A2 cells and also more efficacious in KB-V1 and MCF-7 cells that had been desensitised for doxorubicin. All hydrazones induced apoptosis albeit by slightly different mechanisms. While apoptosis induction by the menthoxymalonyl hydrazone was characterized by an upfront increase in caspase-8 activity, all other hydrazones elicited a hike in caspase-9 activity. Treatment of HL-60 and 518A2 cells with doxorubicin or its heptadecanoyl, linolenoyl, (menthoxycarbonyl)undecanoyl or menthoxymalonyl hydrazones also led to diverging increases of the ratio of bax to bcl-2 mRNA expression, of reactive oxygen species and of mitochondrial membrane damage. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Polyacetal resin composition
  申请人：Harashina Hatsuhiko

  公开号：US20070032605A1

  公开（公告）日：2007-02-08

  A polyacetal resin composition comprises a polyacetal resin, and at least one carboxylic acid hydrazide selected from a saturated or unsaturated long-chain aliphatic carboxylic acid hydrazide, a saturated or unsaturated alicyclic carboxylic acid hydrazide, a dimer acid or trimer acid hydrazide, and an oxycarboxylic acid hydrazide corresponding to each of these hydrazides. The proportion of the carboxylic acid hydrazide may be about 0.001 to 20 parts by weight relative to 100 parts by weight of the polyacetal resin. The polyacetal resin composition may further comprise at least one member selected from an antioxidant, a heat stabilizer, a processing stabilizer, a weather (light)-resistant stabilizer, an impact resistance improver, a slip-improving agent, a coloring agent, and a filler. With the use of such a resin composition, stability of a polyacetal resin is improved, and formaldehyde emission is inhibited.
• RUBBER COMPOSITION AND TIRE
  申请人：OTSUKA CHEMICAL CO., LTD.

  公开号：US20200040167A1

  公开（公告）日：2020-02-06

  A rubber composition comprising a rubber component, a tetrazine compound represented by Formula (1) or a salt thereof: wherein X 1 and X 2 each represent an optionally substituted heterocyclic group, and a processing aid, wherein the rubber component contains a diene rubber obtained by polymerization of monomers including 1,3-butadiene monomer, the diene rubber being present in an amount of 40 parts by mass or more, per 100 parts by mass of the rubber component, and wherein the tetrazine compound or a salt thereof is present in an amount of 0.1 to 10 parts by mass, per 100 parts by mass of the rubber component.