8-deoxyhemigossylic acid dimethyl ether | 168787-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 8-deoxyhemigossylic acid dimethyl ether
• 英文别名: 2,3-Dimethoxy-6-methyl-4-propan-2-ylnaphthalene-1-carboxylic acid
• CAS: 168787-81-3
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: GEDQQQWFMSBNCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-deoxyhemigossylic acid dimethyl ether 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以63%的产率得到2,3-Dihydroxy-4-isopropyl-6-methyl-naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds

  摘要：

  1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC(50) for DDGA was <1 mu M, and its threshold cytotoxicity was approximately 20 mu M. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 mu M. DHGA was ineffective against HN and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 mu M. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.

  DOI：

  10.1021/jm00013a018
• 作为产物：
  描述：

  1-溴-2-异丙基-3,4-二甲氧基苯 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 polyphosphoric ester 、 氢气 、 双氧水 、 溴化乙啶 、 四氯化钛 、 magnesium 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 异丙醇 、 乙腈 、 苯 为溶剂， 25.0~60.0 ℃ 、413.69 kPa 条件下， 反应 32.0h， 生成 8-deoxyhemigossylic acid dimethyl ether
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds

  摘要：

  1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC(50) for DDGA was <1 mu M, and its threshold cytotoxicity was approximately 20 mu M. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 mu M. DHGA was ineffective against HN and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 mu M. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.

  DOI：

  10.1021/jm00013a018

文献信息

• US5780675A
  申请人：——

  公开号：US5780675A

  公开（公告）日：1998-07-14
• US5936120A
  申请人：——

  公开号：US5936120A

  公开（公告）日：1999-08-10
• Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds
  作者：Robert E. Royer、Lorraine M. Deck、Timothy J. Vander Jagt、Francella J. Martinez、Ray G. Mills、Stephen A. Young、David L. Vander Jagt

  DOI：10.1021/jm00013a018

  日期：1995.6

  1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC(50) for DDGA was <1 mu M, and its threshold cytotoxicity was approximately 20 mu M. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 mu M. DHGA was ineffective against HN and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 mu M. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.