2-ethyl-3-methyl-valeryl chloride | 82024-15-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 2-ethyl-3-methyl-valeryl chloride
• 英文别名: 2-Aethyl-3-methyl-valerylchlorid；2-ethyl-3-methyl-pentanoylchloride；α-Ethyl-β-methylvalerylchlorid；2-ethyl-3-methylpentanoyl chloride
• CAS: 82024-15-5
• 化学式: C₈H₁₅ClO
• 分子量: 162.66
• InChiKey: APPZOBDHIFQHIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethyl-3-methyl-valeryl chloride 在 甲胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 2-ethyl-N,3-dimethylpentanamide
  参考文献：
  名称：

  丙戊酸类似物的新型酰胺和尿素衍生物的合成及抗痛觉过敏和抗惊厥活性的评价

  摘要：

  丙戊酸（VPA，1）是主要的广谱抗癫痫药和中枢神经系统药物，广泛用于治疗癫痫，双相情感障碍和偏头痛。VPA的临床使用受到两种严重且危及生命的副作用，致畸性和肝毒性的限制。合成了许多VPA类似物及其酰胺，N-甲基酰胺和尿素衍生物，并在神经性疼痛和癫痫的动物模型中进行了评估。其中，两种酰胺和两种尿素衍生物（1）作为抗神经痛药的效价最高，酰胺（19和20）的ED 50值分别为49和51 mg / kg，尿素衍生物的ED 50值为49和74 mg / kg。 （29和33）。19，20，和29是等效于加巴喷丁，用于治疗神经性疼痛的主要药物。这些数据表明上述新型化合物作为用于治疗神经性疼痛的未来药物开发的候选物的巨大潜力。

  DOI：

  10.1021/jm901229s
• 作为产物：
  描述：

  2-乙基-3-甲基戊酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 2-ethyl-3-methyl-valeryl chloride
  参考文献：
  名称：

  Evaluation of the antiallodynic, teratogenic and pharmacokinetic profile of stereoisomers of valnoctamide, an amide derivative of a chiral isomer of valproic acid

  摘要：

  The purpose of this study was to evaluate the stereoselective pain relieving (antiallodynic) activity, antiallodynic anticonvulsant correlation, teratogenicity and pharmacokinetic profile of two stereoisomers of valnoctamide (VCD). a CNS-active amide derivative of a chiral isomer of valproic acid (VPA). The individual stereoisomers (diastereomers), (2R,3S)-VCD and (2S,3S)-VCD were synthesized and their antiallodynic activity was evaluated in rats using the spinal nerve ligation model of neuropathic pain. The pharmacokinetic profile of the two stereoisomers was evaluated in rats following: 1) i.p. administration of racemic-VCD, 2) i.p. administration of the individual stereoisomers (2R,3S)-VCD and (2S,3S)-VCD. Teratogenicity of racemic-VCD and its two individual stereoisomers was evaluated in a SWV mouse strain known to be highly susceptible to VPA-induced teratogenicity. Racemic-VCD, (2R,35)-VCD and (2S,3S)VCD showed a dose-related reversal of tactile allodynia with ED50 values of 52, 61 and 39 mg/kg, respectively. (2S,35)-VCD was significantly more potent than (2R,3S)-VCD but the opposite is true for its anticonvulsant-effect. In the teratogenicity evaluation racemic-VCD and its two individual stereoisomers showed mild embryotoxicity at doses 7-10 times higher than their antiallodynic-ED50 values, while (2S,3S)-VCD was significantly less embryotoxic than (2R,3S)-VCD and racemic-VCD. Following administration of the racemic-VCD there was an increase in the primary pharmacokinetic parameters of (2S,3S)-VCD but not of (2R,3S)-VCD. This study demonstrates that both racemic-VCD and its stereoisomers show high potency as antiallodynic compounds and possess a wide safety margin. (2S,3S)-VCD is more potent and less embryotoxic than (2R,3S)-VCD and thus, has a potential to become a candidate for development as a new drug for treating neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.neuropharm.2010.03.004

文献信息

• ACYL-UREA DERIVATIVES AND USES THEREOF
  申请人：Bialer Meir

  公开号：US20100280124A1

  公开（公告）日：2010-11-04

  Novel acyl-urea containing compounds, processes of preparing same, compositions containing same and uses thereof in the treatment of neurological diseases and disorders such as epilepsy, neuropathic pain, bipolar disorder, status epilepticus, chemically-induced convulsions and/or seizure disorders, febrile convulsions conditions, metabolic disturbances and a sustenance withdrawal conditions, are provided. Also provided are uses of these and other acyl-urea containing compounds in the treatment of neurological diseases and disorders.

  提供了含有新型酰基脲的化合物、制备该化合物的方法、含有该化合物的组合物以及在治疗神经系统疾病和障碍（如癫痫、神经病性疼痛、躁郁症、持续性癫痫、化学诱导的惊厥和/或癫痫障碍、热性惊厥病症、代谢紊乱和戒断症状）中使用该化合物的方法。还提供了这些和其他含酰基脲的化合物在治疗神经系统疾病和障碍中的用途。
• Acyl-urea derivatives and uses thereof
  申请人：Bialer Meir

  公开号：US08846903B2

  公开（公告）日：2014-09-30

  Novel acyl-urea containing compounds, processes of preparing same, compositions containing same and uses thereof in the treatment of neurological diseases and disorders such as epilepsy, neuropathic pain, bipolar disorder, status epilepticus, chemically-induced convulsions and/or seizure disorders, febrile convulsions conditions, metabolic disturbances and a sustenance withdrawal conditions, are provided. Also provided are uses of these and other acyl-urea containing compounds in the treatment of neurological diseases and disorders.

  提供了含有新型酰基脲的化合物，制备这些化合物的过程，含有这些化合物的组合物以及在治疗神经疾病和疾病方面的用途，如癫痫，神经病痛，躁郁症，癫痫持续状态，化学诱导的惊厥和/或癫痫疾病，发热性惊厥症状，代谢紊乱和戒断症状。此外，还提供了这些和其他含有酰基脲的化合物在治疗神经疾病和疾病方面的用途。
• Syntheses and Evaluation of Anticonvulsant Profile and Teratogenicity of Novel Amide Derivatives of Branched Aliphatic Carboxylic Acids with 4-Aminobenzensulfonamide
  作者：Naama Hen、Meir Bialer、Bogdan Wlodarczyk、Richard H. Finnell、Boris Yagen

  DOI：10.1021/jm100170w

  日期：2010.5.27

  Despite the availability of 14 new antiepileptic drugs (AEDs), about 30% of epileptic patients are not seizure-free. Consequently there is substantial need to develop new effective AEDs. A novel class of aromatic amides composed of phenylacetic acid or branched aliphatic carboxylic acids, with five to nine carbons in their carboxylic moiety, and aminobenzenesulfonamide were synthesized and evaluated in the anticonvulsant rat-maximal electroshock (MES) and subcutaneous metrazol seizure (scMet) tests. Fourteen of the synthesized amides had an anticonvulsant ED(50) of <50 mg/kg in the rat-MES test. The amides 2-methyl-N-(4-sulfamoylphenyl)butyramide (10), 2-ethyl-N-(4-sulfamoylphenyl)butyramide (11), and 3,3-dimethyl-N-(4-sulfamoylphenyl)butyramide (15) were the most potent compounds possessing MES-ED(50) values of 7.6, 9.9, and 9.4 mg/kg and remarkable protective index (PI = TD(50)/ ED(50)) values of 65.7, 50.5, and 53.2, respectively. These potent sulfanylamides caused neural tube defects only at doses markedly exceeding their effective dose. The anticonvulsant properties of these compounds make them potential candidates for further development as new, potent, and safe AEDs.
• WO2009/1356
  申请人：——

  公开号：——

  公开（公告）日：——
• Some Alkyl and Aryl Amides and Ureides as Hypnotics¹
  作者：E. H. Volwiler、D. L. Tabern

  DOI：10.1021/ja01299a012

  日期：1936.8