6-bromo-2,3-dimethoxy-7-methyl-1-(1-methylethyl)naphthalene | 168787-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-2,3-dimethoxy-7-methyl-1-(1-methylethyl)naphthalene
• 英文别名: 7-Bromo-2,3-dimethoxy-6-methyl-4-(1-methylethyl)naphthalene；6-bromo-2,3-dimethoxy-7-methyl-1-propan-2-ylnaphthalene
• CAS: 168787-77-7
• 化学式: C₁₆H₁₉BrO₂
• 分子量: 323.23
• InChiKey: JQIOBBDROTUGBN-UHFFFAOYSA-N

物化性质

• 沸点：
  404.0±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-2,3-dimethoxy-7-methyl-1-(1-methylethyl)naphthalene 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 氢气 、 四氯化钛 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 5.25h， 生成 7-Benzyl-4-isopropyl-2,3-dimethoxy-6-methyl-naphthalene-1-carbaldehyde
  参考文献：
  名称：

  Selective Inhibitors of Human Lactate Dehydrogenases and Lactate Dehydrogenase from the Malarial Parasite Plasmodium falciparum

  摘要：

  Derivatives of the sesquiterpene 8-deoxyhemigossylic acid (2,3-dihydroxy-6-methyl-4-(1-methylethyl)-1-naphthoic acid) were synthesized that contained altered alkyl groups in the 4-position and contained alkyl or aralkyl groups in the 7-position. These substituted dihydroxynaphthoic acids are selective inhibitors of human lactate dehydrogenase-H (LDHH) and LDH-M and of lactate dehydrogenase from the malarial parasite Plasmodium falciparum (pLDH). All inhibitors are competitive with the binding of NADH. Selectivity for LDH-H, LDH-M, or pLDH is strongly dependent upon the groups that are in the 4- and 7-positions of the dihydroxynaphthoic acid backbone. Dissociation constants as low as 50 nM were observed, with selectivity as high as 400-fold.

  DOI：

  10.1021/jm980334n
• 作为产物：
  描述：

  4-<3,4-dimethoxy-2-(1-methylethyl)phenyl>-3-methylbutanoic acid 在 sodium tetrahydroborate 、 polyphosphoric ester 、 溴 、 N,N-二甲基甲酰胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 异丙醇 、 苯 为溶剂， 反应 5.0h， 生成 6-bromo-2,3-dimethoxy-7-methyl-1-(1-methylethyl)naphthalene
  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

• Deoxygossylic compounds
  申请人：The University of New Mexico

  公开号：US05780675A1

  公开（公告）日：1998-07-14

  The invention provides deoxygossylic compounds having useful biological activities, and methods for the synthesis of these and related compounds. The invention further provides valuable intermediates for the synthesis of the compounds, and pharmaceutical compositions containing biologically active compounds according to the invention.

  本发明提供了具有有用生物活性的脱氧高丝氨酸化合物，以及这些化合物及相关化合物的合成方法。本发明还提供了用于合成这些化合物的有价值的中间体，以及包含根据本发明的生物活性化合物的制药组合物。
• 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.
• Selective Inhibitors of Human Lactate Dehydrogenases and Lactate Dehydrogenase from the Malarial Parasite <i>Plasmodium</i> <i>f</i><i>alciparum</i>
  作者：Lorraine M. Deck、Robert E. Royer、Brian B. Chamblee、Valerie M. Hernandez、Richard R. Malone、Jose E. Torres、Lucy A. Hunsaker、Robert C. Piper、Michael T. Makler、David L. Vander Jagt

  DOI：10.1021/jm980334n

  日期：1998.9.1

  Derivatives of the sesquiterpene 8-deoxyhemigossylic acid (2,3-dihydroxy-6-methyl-4-(1-methylethyl)-1-naphthoic acid) were synthesized that contained altered alkyl groups in the 4-position and contained alkyl or aralkyl groups in the 7-position. These substituted dihydroxynaphthoic acids are selective inhibitors of human lactate dehydrogenase-H (LDHH) and LDH-M and of lactate dehydrogenase from the malarial parasite Plasmodium falciparum (pLDH). All inhibitors are competitive with the binding of NADH. Selectivity for LDH-H, LDH-M, or pLDH is strongly dependent upon the groups that are in the 4- and 7-positions of the dihydroxynaphthoic acid backbone. Dissociation constants as low as 50 nM were observed, with selectivity as high as 400-fold.