4-(2,2-dimethyl-1-oxopropyl)-benzamide | 167760-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,2-dimethyl-1-oxopropyl)-benzamide
• 英文别名: 4-(2,2-dimethylpropanoyl)benzamide
• CAS: 167760-01-2
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: YVJNRRUMRWRMMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2,2-dimethyl-1-oxopropyl)-benzamide 在 potassium hydride 、 三氟乙酸 作用下， 反应 26.25h， 生成 2-[Bis[4-(2,2-dimethylpropanoyl)benzoyl]amino]acetic acid
  参考文献：
  名称：

  Hypoglycemic Prodrugs of 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid

  摘要：

  SAH 51-641 (1) is a potent hypoglycemic agent, which acts by inhibiting hepatic gluconeogenesis. It is a prodrug of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid (2) and 4-(2,2-dimethyl-1-hydroxy propyl)benzoic acid (3), which sequester coenzyme A (CoA) in the mitochondria, and inhibits medium-chain acyltransferase. 1-3 and 4-tert-butylbenzoic acid all cause testicular degeneration in rats at pharmacologically active doses. 14b (FOX 988) is a prodrug of 3, which is metabolized in the liver at a rate sufficient enough to have hypoglycemic potency (an ED50 of 65 mu mol/kg, 28 mg/kg/day, for glucose lowering), yet by avoiding significant escape of the metabolite 3 to the systemic circulation, it avoids the testicular toxicity at doses up to 1500 mu mol/kg/day. 14b was selected for clinical studies.

  DOI：

  10.1021/jm980438y
• 作为产物：
  描述：

  2,2-二甲基-1-(4-甲基苯基)丙-1-酮 在 ammonium hydroxide 、 potassium permanganate 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 6.5h， 生成 4-(2,2-dimethyl-1-oxopropyl)-benzamide
  参考文献：
  名称：

  Hypoglycemic Prodrugs of 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid

  摘要：

  SAH 51-641 (1) is a potent hypoglycemic agent, which acts by inhibiting hepatic gluconeogenesis. It is a prodrug of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid (2) and 4-(2,2-dimethyl-1-hydroxy propyl)benzoic acid (3), which sequester coenzyme A (CoA) in the mitochondria, and inhibits medium-chain acyltransferase. 1-3 and 4-tert-butylbenzoic acid all cause testicular degeneration in rats at pharmacologically active doses. 14b (FOX 988) is a prodrug of 3, which is metabolized in the liver at a rate sufficient enough to have hypoglycemic potency (an ED50 of 65 mu mol/kg, 28 mg/kg/day, for glucose lowering), yet by avoiding significant escape of the metabolite 3 to the systemic circulation, it avoids the testicular toxicity at doses up to 1500 mu mol/kg/day. 14b was selected for clinical studies.

  DOI：

  10.1021/jm980438y

文献信息

• Benzoic acid derivatives as antidiabetic agents
  申请人：Sandoz Ltd.

  公开号：US05378728A1

  公开（公告）日：1995-01-03

  Compound of the formula ##STR1## where R is CH.sub.3 (CH.sub.2).sub.m, A and B are hydrogen, a bond or --(CH.sub.2).sub.n, X is ##STR2## m is 0, 1 , 2 or 3, n is 1 , 2, or 3, R.sub.1 is hydrogen or lower alkyl, and Y is --OH, --OR.sub.2 or --NR.sub.3 R.sub.4 where R.sub.2, R.sub.3 and R.sub.4 are hydrogen or unsubstituted or substituted alkyl, aryl and aralkyl substituents.

  化合物的公式为##STR1##其中R为CH.sub.3(CH.sub.2).sub.m，A和B为氢、一个键或--(CH.sub.2).sub.n，X为##STR2##m为0、1、2或3，n为1、2或3，R.sub.1为氢或较低的烷基，Y为--OH、--OR.sub.2或--NR.sub.3R.sub.4，其中R.sub.2、R.sub.3和R.sub.4为氢或未取代或取代的烷基、芳基和芳基烷基取代基。
• Alpha- and beta-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
  申请人：Vazquez L. Michael

  公开号：US20070078173A1

  公开（公告）日：2007-04-05

  α- and β-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.

  α-和β-氨基酸羟乙基氨磺酰胺化合物可作为逆转录病毒蛋白酶抑制剂，特别是作为HIV蛋白酶的抑制剂。
• ALPHA- AND BETA-AMINO ACID HYDROXYETHYLAMINO SULFONAMIDES USEFUL AS RETROVIRAL PROTEASE INHIBITORS
  申请人：Vazquez Michael L.

  公开号：US20090023664A1

  公开（公告）日：2009-01-22

  α- and β-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.

  α-和β-氨基酸羟乙基氨磺酰胺化合物是有效的逆转录病毒蛋白酶抑制剂，特别是作为HIV蛋白酶的抑制剂。
• US5378728A
  申请人：——

  公开号：US5378728A

  公开（公告）日：1995-01-03
• US7320983B2
  申请人：——

  公开号：US7320983B2

  公开（公告）日：2008-01-22