2-正丙基-4-戊炔酸 | 24102-11-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-正丙基-4-戊炔酸
• 英文名称: (+/-)-2-n-propyl-4-pentynoic acid
• 英文别名: 2-propyl-4-pentynoic acid；4-yne-valproic acid；4-yne-VPA；4ynVPA；2-propyl-pent-4-ynoic acid；2-n-propyl-4-pentynoic acid；2-propylpent-4-ynoic acid
• CAS: 24102-11-2
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: KWBNQXQUIZBELR-UHFFFAOYSA-N

物化性质

• 沸点：
  234.8±23.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  2-正丙基-4-戊炔酸 在 水 、 mercury(II) sulfate 作用下， 生成 4-氧代-2-丙基戊酸
  参考文献：
  名称：

  丙戊酸的十二种类似物的抗惊厥和神经毒性活性。

  摘要：

  测试了十二种抗癫痫药丙戊酸（VPA）的外消旋类似物，并通过皮下戊四氮（PTZ）癫痫发作阈值测试与VPA进行了比较，研究了其抗惊厥活性，并通过旋翼仪测试了其神经毒性。四种化合物以对VPA等摩尔剂量（1.5 mmol / kg）产生最大的抗惊厥活性（100％保护），两种化合物在较低剂量（1.0 mmol / kg）下显示出相似的作用。四种化合物产生较低的活性（38-80％的保护作用），两种化合物在所用剂量（1.5 mmol / kg）下无抗惊厥活性。12种化合物中的两种，（+/-）-2-n-丙基-4-己酸（11）和（+/-）-4-甲基-2-正丙基-4-戊烯酸（12），在产生最大抗惊厥作用的剂量下无镇静作用。我们首次成功开发出两种具有比VPA更高的保护指数和安全比的化合物。化合物11的作用时间更长，保护指数更高，但安全系数却比12低。这些化合物的抗惊厥作用和最小的神经毒性与其计算的亲脂性（C log

  DOI：

  10.1002/jps.2600821214
• 作为产物：
  描述：

  丙基丙二酸二乙酯 在 氢氧化钾 、 sodium ethanolate 作用下， 以 乙醇 、 水 为溶剂， 生成 2-正丙基-4-戊炔酸
  参考文献：
  名称：

  Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect

  摘要：

  In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant-activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds, These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (+/-)-4-methyl-2-n-propyl-4-pentenoic acid and (+/-)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.

  DOI：

  10.1021/tx950216s

文献信息

• GLYCOSYLATED VALPROIC ACID ANALOGS AND USES THEREOF
  申请人：HEYMAN Norman S.

  公开号：US20130029924A1

  公开（公告）日：2013-01-31

  Glycosylated valproic acid and its analogs are provided. In some embodiments, the glycosylated valproic acid and its analogs have improved solubility and are ideal for drug delivery to treat a variety of diseases.

  提供了糖基化的丙戊酸及其类似物。在某些实施方式中，糖基化的丙戊酸及其类似物具有改善的溶解性，并且非常适合用于药物输送以治疗各种疾病。
• Valproic acid analogues and pharmaceutical composition thereof
  申请人：Abbott Slade Frank

  公开号：US20060223888A1

  公开（公告）日：2006-10-05

  Analogues of valproic acid useful in treating neuroaffective disorders including convulsions, bipolar disorder, and migraine headache are disclosed. The analogues are halide liver substituted analogues, cyclic analogues, and conjugated diene analogues of valproic acid. Pharmaceutical compositions or prodrugs containing the analogues or pharmaceutically acceptable salts thereof are disclosed. Methods of malting the compounds and treating mammals with neuroaffective disorders are also disclosed.

  本文介绍了一类与丙戊酸类似的化合物，可用于治疗神经情感障碍，包括惊厥、双相障碍和偏头痛。这些类似物是丙戊酸的卤代肝脏取代类似物、环状类似物和共轭二烯类似物。本文还介绍了含有这些类似物或其药学上可接受的盐的药物组合物或前药。同时，本文还介绍了制备这些化合物和治疗患有神经情感障碍的哺乳动物的方法。
• Valproic acid and derivatives thereof for the combination therapy of human cancers, for the treatment of tumour metastasis and minimal residual disease
  申请人：G2M Cancer Drugs AG

  公开号：EP1293205A1

  公开（公告）日：2003-03-19

  The present invention relates to the use of the drug valproic acid and derivatives thereof as inhibitors of enzymes having histone deacetylase activity for the therapeutic treatment of human cancers in combination with established therapeutic principles. The invention also relates to the use of those compounds for the treatment of tumor metastasis and minimal residual disease. The invention includes the manufacture of a clinically used substance for the treatment of human cancers.

  本发明涉及将药物丙戊酸及其衍生物作为具有组蛋白去乙酰化酶活性的酶的抑制剂，结合既定的治疗原则用于人类癌症的治疗。本发明还涉及使用这些化合物治疗肿瘤转移和最小残留病。本发明包括制造临床上用于治疗人类癌症的物质。
• Valproic acid for a combination treatment of human cancers, tumor metastasis and minimal residual disease
  申请人：G2M Cancer Drugs AG

  公开号：EP1529527A2

  公开（公告）日：2005-05-11

  The present invention relates to the use of the drug valproic acid and derivatives thereof as inhibitors of enzymes having histone deacetylase activity for the sensitizing treatment of human cancers in combination with established therapeutic principles. The invention also relates to the use of those compounds for the treatment of tumor metastasis and minimal residual disease. The invention includes the manufacture of a clinically used substance for the treatment of human cancers.

  本发明涉及使用药物丙戊酸及其衍生物作为具有组蛋白去乙酰化酶活性的酶的抑制剂，结合既定的治疗原则对人类癌症进行增敏治疗。本发明还涉及使用这些化合物治疗肿瘤转移和最小残留病。本发明包括制造临床上用于治疗人类癌症的物质。
• Valproic acid and derivatives for the sensitisation of human cancer cells to increase efficacy in a combination therapy
  申请人：G2M Cancer Drugs AG

  公开号：EP1602371A2

  公开（公告）日：2005-12-07

  The present invention relates to the use of the drug valporic acid and derivatives thereof as inhibitors of enzymes having histone deacetylase activity for the manufacture of a medicament to sensitize human cancer cells for treatment efficacy in combination with clinically established anti-cancer therapeutic drugs. The invention also relates to the treatment of tumor metastasis and minimal residual disease.

  本发明涉及将药物戊硼酸及其衍生物作为具有组蛋白去乙酰化酶活性的酶的抑制剂，用于制造一种药物，使人类癌细胞与临床上已确定的抗癌治疗药物结合使用，以获得治疗效果。本发明还涉及肿瘤转移和最小残留病的治疗。