(3aα,4β,8α,8aβ)-3,3'-[(dihydro-2,2-dimethyl-6-oxo-4,8-bis(phenylmethyl)-4H-1,3-dioxolo[4,5-e][1,3]diazepine-5,7(6H,8H)-diyl)bis(methylene)]bis[benzoic acid] | 183860-59-5

• 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: (3aα,4β,8α,8aβ)-3,3'-[(dihydro-2,2-dimethyl-6-oxo-4,8-bis(phenylmethyl)-4H-1,3-dioxolo[4,5-e][1,3]diazepine-5,7(6H,8H)-diyl)bis(methylene)]bis[benzoic acid]
• 英文别名: 3-[[(3aS,4R,8R,8aS)-4,8-dibenzyl-5-[(3-carboxyphenyl)methyl]-2,2-dimethyl-6-oxo-3a,4,8,8a-tetrahydro-[1,3]dioxolo[4,5-e][1,3]diazepin-7-yl]methyl]benzoic acid
• CAS: 183860-59-5
• 化学式: C₃₈H₃₈N₂O₇
• 分子量: 634.729
• InChiKey: LNGXSUWDQUHCFS-WZJLIZBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aα,4β,8α,8aβ)-3,3'-[(dihydro-2,2-dimethyl-6-oxo-4,8-bis(phenylmethyl)-4H-1,3-dioxolo[4,5-e][1,3]diazepine-5,7(6H,8H)-diyl)bis(methylene)]bis[benzoic acid] 在 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 3-[[(3aS,4R,8R,8aS)-4,8-dibenzyl-2,2-dimethyl-6-oxo-5-[[3-[[5-(trifluoromethyl)pyridin-2-yl]carbamoyl]phenyl]methyl]-3a,4,8,8a-tetrahydro-[1,3]dioxolo[4,5-e][1,3]diazepin-7-yl]methyl]-N-[5-(trifluoromethyl)pyridin-2-yl]benzamide
  参考文献：
  名称：

  HIV Protease Inhibitory Bis-benzamide Cyclic Ureas:  A Quantitative Structure−Activity Relationship Analysis

  摘要：

  A series of N,N'-disubstituted cyclic urea 3-benzamides has been synthesized and evaluated for HIV protease inhibition and antiviral activity. Some of these benzamides have been shown to be potent inhibitors of HIV protease with K-i < 0.050 nM and IC90 < 20 nM for viral replication and, as such, may be useful in the treatment of AIDS. The synthesis and quantitative structure-activity relationship for this benzamide series will be discussed.

  DOI：

  10.1021/jm9602773
• 作为产物：
  描述：

  (4R,5S,6S,7R)-hexahydro-5,6-O-isopropylidene-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-one 在 sodium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.5h， 生成 (3aα,4β,8α,8aβ)-3,3'-[(dihydro-2,2-dimethyl-6-oxo-4,8-bis(phenylmethyl)-4H-1,3-dioxolo[4,5-e][1,3]diazepine-5,7(6H,8H)-diyl)bis(methylene)]bis[benzoic acid]
  参考文献：
  名称：

  HIV Protease Inhibitory Bis-benzamide Cyclic Ureas:  A Quantitative Structure−Activity Relationship Analysis

  摘要：

  A series of N,N'-disubstituted cyclic urea 3-benzamides has been synthesized and evaluated for HIV protease inhibition and antiviral activity. Some of these benzamides have been shown to be potent inhibitors of HIV protease with K-i < 0.050 nM and IC90 < 20 nM for viral replication and, as such, may be useful in the treatment of AIDS. The synthesis and quantitative structure-activity relationship for this benzamide series will be discussed.

  DOI：

  10.1021/jm9602773

文献信息

• Nonsymmetrically Substituted Cyclic Urea HIV Protease Inhibitors
  作者：Wendell W. Wilkerson、Scott Dax、Walter W. Cheatham

  DOI：10.1021/jm970288b

  日期：1997.12.1

  A series of nonsymmetrically substituted cyclic ureacarboxamides was synthesized and evaluated for antiviral activity as a function of the inhibition of HIV-protease. Selected protease inhibitors were also evaluated for oral bioavailability. The synthesis, pharmacology, quantitative structure-activity relationship (QSAR), and pharmacokinetics for the series will be discussed.

  合成了一系列非对称取代的环状脲羧酰胺，并评估了其抗病毒活性与抑制HIV蛋白酶的关系。还评估了选定的蛋白酶抑制剂的口服生物利用度。将讨论该系列的合成，药理学，定量构效关系（QSAR）和药代动力学。
• HIV Protease Inhibitory Bis-benzamide Cyclic Ureas:  A Quantitative Structure−Activity Relationship Analysis
  作者：Wendell W. Wilkerson、Emeka Akamike、Walter W. Cheatham、Andrea Y. Hollis、R. Dale Collins、Indawati DeLucca、Patrick Y. S. Lam、Yu Ru

  DOI：10.1021/jm9602773

  日期：1996.1.1

  A series of N,N'-disubstituted cyclic urea 3-benzamides has been synthesized and evaluated for HIV protease inhibition and antiviral activity. Some of these benzamides have been shown to be potent inhibitors of HIV protease with K-i < 0.050 nM and IC90 < 20 nM for viral replication and, as such, may be useful in the treatment of AIDS. The synthesis and quantitative structure-activity relationship for this benzamide series will be discussed.