N,N-dibenzylmalonamic acid | 1208236-40-1

• 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: N,N-dibenzylmalonamic acid
• 英文别名: Malonic acid dibenzylamide；3-(dibenzylamino)-3-oxopropanoic acid
• CAS: 1208236-40-1
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: AQZKADMJLAZWMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dibenzylmalonamic acid 、 3-羟基苯甲酸苄酯 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52%的产率得到benzyl 3-[2-(N,N-dibenzylaminocarbonyl)-ethanoyl]-oxybenzoate
  参考文献：
  名称：

  Substituted aryl malonamates as new serine β-lactamase substrates: Structure–activity studies

  摘要：

  A series of substituted aryl malonamates have been prepared. These compounds are analogues of aryl phenaceturates where the amido side chain has been replaced by a retro-amide. Like the phenaceturates, these compounds are substrates of typical class A and class C beta-lactamases, particularly of the latter, and of soluble DD-peptidases. The effect of substituents alpha to the ester carbonyl group on turnover by these enzymes is similar to that in the phenaceturates. On the other hand, N-alkylation of the side chain amide of malonamates, but not of phenaceturates, retains the susceptibility of the compounds to hydrolysis by beta-lactamases. This reactivity is not enhanced, however, by bridging the amide nitrogen and C alpha atoms. A phosphonate analogue of the malonamates was found to be an irreversible inhibitor of the beta-lactamases. These results, therefore, provide further evidence for the covalent access of compounds bearing retroamide side chains to the active sites of beta-lactam-recognizing enzymes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.056
• 作为产物：
  描述：

  丙酸,3-[二(苯基甲基)氨基]-3-羰基-,甲基酯 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以78%的产率得到N,N-dibenzylmalonamic acid
  参考文献：
  名称：

  Substituted aryl malonamates as new serine β-lactamase substrates: Structure–activity studies

  摘要：

  A series of substituted aryl malonamates have been prepared. These compounds are analogues of aryl phenaceturates where the amido side chain has been replaced by a retro-amide. Like the phenaceturates, these compounds are substrates of typical class A and class C beta-lactamases, particularly of the latter, and of soluble DD-peptidases. The effect of substituents alpha to the ester carbonyl group on turnover by these enzymes is similar to that in the phenaceturates. On the other hand, N-alkylation of the side chain amide of malonamates, but not of phenaceturates, retains the susceptibility of the compounds to hydrolysis by beta-lactamases. This reactivity is not enhanced, however, by bridging the amide nitrogen and C alpha atoms. A phosphonate analogue of the malonamates was found to be an irreversible inhibitor of the beta-lactamases. These results, therefore, provide further evidence for the covalent access of compounds bearing retroamide side chains to the active sites of beta-lactam-recognizing enzymes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.056

文献信息

• NOVEL LACTOSAMINE DERIVATIVES
  申请人：Glycom APS

  公开号：EP1996602B1

  公开（公告）日：2011-02-16
• [EN] AMIDE ESTER ACAT INHIBITORS
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1991015464A1

  公开（公告）日：1991-10-17

  (EN) Pharmaceutically useful compounds having acylcoenzyme A: cholesterol acyltransferase inhibitory activity having general formula (I) wherein each of m and n is zero, one or two; X is oxygen or sulfur and each of R1, R2, R3, R4, and R5 is hydrogen or a hydrocarbon substituent.(FR) Composés pharmaceutiquement utiles présentant une activité inhibant l'acyle-coenzyme A: cholestérol acyltransférase ayant la formule générale (I), dans laquelle m et n représentent chacun 0, 1 ou 2; X représente de l'oxygène ou du soufre et R1, R2, R3, R4 et R5 représentent chacun de l'hydrogène ou un substituant hydrocarbure.