2,2-dimethyl-N-(4-sulfamoyl-benzyl)-propionamide | 547705-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dimethyl-N-(4-sulfamoyl-benzyl)-propionamide
• 英文别名: N-(4-Sulfamoylbenzyl)Pivalamide；2,2-dimethyl-N-[(4-sulfamoylphenyl)methyl]propanamide
• CAS: 547705-80-6
• 化学式: C₁₂H₁₈N₂O₃S
• mdl: MFCD01475657
• 分子量: 270.353
• InChiKey: OLVQEUVZKPOXJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  磺胺米隆 、 三甲基乙酰氯 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 2,2-dimethyl-N-(4-sulfamoyl-benzyl)-propionamide
  参考文献：
  名称：

  Syntheses and Evaluation of Anticonvulsant Profile and Teratogenicity of Novel Amide Derivatives of Branched Aliphatic Carboxylic Acids with 4-Aminobenzensulfonamide

  摘要：

  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.

  DOI：

  10.1021/jm100170w

文献信息

• [EN] SULFANYLAMIDE DERIVATIVES, USES THEREOF AND COMPOSITIONS COMPRISING THEM<br/>[FR] DÉRIVÉS DE SULFANYLAMIDE, LEURS UTILISATIONS ET COMPOSITIONS LES CONTENANT
  申请人：YISSUM RES DEV CO

  公开号：WO2011033518A1

  公开（公告）日：2011-03-24

  The present invention concerns a family of sulfanilamide derivatives of formula (I) as anticonvulsant agents, where R1 is selected from optionally substituted C4-C9 alkyl, optionally substituted C6-C10 aryl, optionally substituted C6-C10 alkylenearyl and optionally substituted C5-C10 heteroaryl; R2 is selected from -H and optionally substituted C1-C6 alkyl; each of R3 and R4, independently of each other, is selected from -H, optionally substituted C1-C6 alkyl, optionally substituted C6-C10 aryl and optionally substituted C5-C10 heteroaryl; n is 0, 1, 2, 3 or 4. The derivatives have been prepared and their anticonvulsant profile was evaluated for the control of epileptic seizures.

  本发明涉及一类磺胺基苯甲酰胺衍生物，其化学式为(I)，作为抗癫痫药物，其中R1选自可选取的取代的C4-C9烷基、可选取的取代的C6-C10芳基、可选取的取代的C6-C10烷基芳基和可选取的取代的C5-C10杂环芳基；R2选自-H和可选取的取代的C1-C6烷基；R3和R4中的每一个，独立地选自-H、可选取的取代的C1-C6烷基、可选取的取代的C6-C10芳基和可选取的取代的C5-C10杂环芳基；n为0、1、2、3或4。这些衍生物已经制备，并评估了它们的抗癫痫特性以控制癫痫发作。
• SULFANYLAMIDE DERIVATIVES, USES THEREOF AND COMPOSITIONS COMPRISING THEM
  申请人：Yissum Research Development Company of the Hebrew University of Jerusalem, Ltd.

  公开号：EP2480527A1

  公开（公告）日：2012-08-01
• US7223738B2
  申请人：——

  公开号：US7223738B2

  公开（公告）日：2007-05-29