2-isopropyl-3-methylpentanamide | 1196996-43-6

• 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: 2-isopropyl-3-methylpentanamide
• 英文别名: sec-butylisopropylacetamide；3-Methyl-2-propan-2-ylpentanamide
• CAS: 1196996-43-6
• 化学式: C₉H₁₉NO
• 分子量: 157.256
• InChiKey: ZLSITYMRUSNQID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基戊酸 在 ammonium hydroxide 、 氯化亚砜 、 lithium diisopropyl amide 作用下， 生成 2-isopropyl-3-methylpentanamide
  参考文献：
  名称：

  Pharmacodynamic and pharmacokinetic analysis of CNS-active constitutional isomers of valnoctamide and sec-butylpropylacetamide — Amide derivatives of valproic acid

  摘要：

  Valnoctamide (VCD) and sec-butylpropylacetamide (SPD) are CNS-active closely related amide derivatives of valproic acid with unique anticonvulsant activity. This study evaluated how small chemical changes affect the pharmacodynamics (PD; anticonvulsant activity and teratogenicity) and pharmacokinetics (PK) of three constitutional isomers of SPD [sec-butylisopropylacetamide (SID) and tert-butylisopropylacetamide (TID)] and of VCD [tert-butylethylacetamide (TED)]. The anticonvulsant activity of SID, TID, and TED was comparatively evaluated in several rodent anticonvulsant models. The PK-PD relationship of SID, TID, and TED was evaluated in rats, and their teratogenicity was evaluated in a mouse strain highly susceptible to teratogen-induced neural tube defects (NTDs). sec-Butylisopropylacetamide and TID have a similar PK profile to SPD which may contribute to their similar anticonvulsant activity. tert-Butylethylacetamide had a better PK profile than VCD (and SPD); however, this did not lead to a superior anticonvulsant activity. sec-Butylisopropylacetamide and TED did not cause NTDs at doses 4-7 times higher than their anticonvulsant ED50 values. In rats, SID, TID (ip), and TED exhibited a broad spectrum of anticonvulsant activity. However, combined anticonvulsant analysis in mice and rats shows SID as the most potent compound with similar activity to that of SPD, demonstrating that substitution of the isobutyl moiety in the SPD or VCD molecule by tert-butyl as well as a propyl-to-isopropyl replacement in the SPD molecule did not majorly affect the anticonvulsant activity. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.yebeh.2015.02.040

文献信息

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING PROTEIN EMBRYONIC ECTODERM DEVELOPMENT ACTIVITY AND TREATING DISEASE<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR L'INHIBITION DE L'ACTIVITÉ DE DÉVELOPPEMENT D'ECTODERME EMBRYONNAIRE DE PROTÉINE ET DE TRAITEMENT D'UNE MALADIE
  申请人：EXO THERAPEUTICS INC

  公开号：WO2021195183A1

  公开（公告）日：2021-09-30

  The invention provides compounds that are inhibitors of the protein embryonic ectoderm development (EED), pharmaceutical compositions, their use in modulating the activity of EED, and their use in the treatment of medical disorders, such as cancer. The invention further provides methods of treating medical disorders, such as cancer, and covalently modifying and/or modulating the activity of EED, using an agent that reacts with, and forms a covalent bond to, cysteine324 of EED.

  这项发明提供了抑制蛋白胚胎外胚层发育（EED）的化合物，药物组合物，它们在调节EED活性中的应用，以及它们在治疗癌症等医学疾病中的应用。该发明还提供了治疗医学疾病（如癌症）的方法，并利用一种与EED的半胱氨酸324发生反应并形成共价键的试剂，对EED进行共价修饰和/或调节活性。
• Synthesis and Evaluation of Antiallodynic and Anticonvulsant Activity of Novel Amide and Urea Derivatives of Valproic Acid Analogues
  作者：Dan Kaufmann、Meir Bialer、Jakob Avi Shimshoni、Marshall Devor、Boris Yagen

  DOI：10.1021/jm901229s

  日期：2009.11.26

  Valproic acid (VPA, 1) is a major broad spectrum antiepileptic and central nervous system drug widely used to treat epilepsy, bipolar disorder, and migraine. VPA’s clinical use is limited by two severe and life-threatening side effects, teratogenicity and hepatotoxicity. A number of VPA analogues and their amide, N-methylamide and urea derivatives, were synthesized and evaluated in animal models of

  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。
• [EN] MENTHOL DERIVATIVE AND COOLING AGENT COMPOSITION COMPRISING THE SAME<br/>[FR] DÉRIVÉ DU MENTHOL ET COMPOSITION D'AGENT RAFRAÎCHISSANT COMPRENANT CELUI-CI
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2005115325A1

  公开（公告）日：2005-12-08

  The invention relates to innovative menthol derivatives which are represented by the general formula (I) below and are excellent in a cooling effect and cool retaining effect, cooling agent compositions comprising the menthol derivatives, and sensory stimulation agent compositions containing the cooling agent compositions, as well as fragrance compositions, beverage or food products, cosmetic products, toiletry products, bathing agents, and pharmaceutical products containing the cooling agent compositions or sensory stimulation agent compositions. (general formula (I)) wherein R1 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an acyl group having 1 to 5 carbon atoms; R2 and R3 independently represent an alkylene group having 2 to 5 carbon atoms and optionally having a substituent; double dotted line represents a single bond or a double bond; and n is an integer of 1 to 3.

  该发明涉及创新的薄荷醇衍生物，其由下面的通用式（I）表示，具有出色的降温效果和保持冷却效果，包括薄荷醇衍生物的冷却剂组合物，以及含有冷却剂组合物的感官刺激剂组合物，还包括含有冷却剂组合物或感官刺激剂组合物的香精组合物、饮料或食品产品、化妆品、洗涤用品、沐浴剂和含有冷却剂组合物或感官刺激剂组合物的药品产品。（通用式（I））其中R1代表氢原子、具有1至4个碳原子的烷基基团或具有1至5个碳原子的酰基基团；R2和R3独立地代表具有2至5个碳原子且可选地具有取代基的烷基基团；双点线代表单键或双键；n为1至3的整数。
• MENTHOL DERIVATIVE AND COOLING AGENT COMPOSITION COMPRISING THE SAME
  申请人：Takasago International Corporation

  公开号：EP1761238A1

  公开（公告）日：2007-03-14
• VANILLIN ACETALS AND SENSORY STIMULANT COMPOSITION CONTAINING THE SAME
  申请人：Takasago International Corporation

  公开号：EP1902043A1

  公开（公告）日：2008-03-26