2-methyl-N⁴-[3-(1-pyrrolidinyl)propyl]-1,4-benzenediamine | 329943-39-7

• 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: 2-methyl-N⁴-[3-(1-pyrrolidinyl)propyl]-1,4-benzenediamine
• 英文别名: 2-Methyl-n4-[3-(1-pyrrolidinyl)propyl]-1,4-benzenediamine；2-methyl-4-N-(3-pyrrolidin-1-ylpropyl)benzene-1,4-diamine
• CAS: 329943-39-7
• 化学式: C₁₄H₂₃N₃
• mdl: MFCD11848920
• 分子量: 233.357
• InChiKey: KTNYSUAONSJHFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  41.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-N⁴-[3-(1-pyrrolidinyl)propyl]-1,4-benzenediamine 、 [4-chloro-2-(3,5-difluorobenzoyl)phenoxy]acetyl chloride 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以0.064 g的产率得到2-[4-chloro-2-(3,5-difluorobenzoyl)phenoxy]-N-[2-methyl-4-(3-pyrrolidin-1-ylpropylamino)phenyl]acetamide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Benzophenones Leading to the Discovery of a Potent, Next Generation HIV Nonnucleoside Reverse Transcriptase Inhibitor

  摘要：

  Despite the progress of the past two decades, there is still considerable need for safe, efficacious drugs that target human immunodeficiency virus (HIV). This is particularly true for the growing number of patients infected with virus resistant to currently approved HIV drugs. Our high throughput screening effort identified a benzophenone template as a potential nonnucleoside reverse transcriptase inhibitor (NNRTI). This manuscript describes our extensive exploration of the benzophenone structure-activity relationships, which culminated in the identification of several compounds with very potent inhibition of both wild type and clinically relevant NNRTI-resistant mutant strains of HIV. These potent inhibitors include 70h (GW678248), which has in vitro antiviral assay IC50 values of 0.5 nM against wild-type HIV, 1 nM against the K103N mutant associated with clinical resistance to efavirenz, and 0.7 nM against the Y181C mutant associated with clinical resistance to nevirapine. Compound 70h has also demonstrated relatively low clearance in intravenous pharmacokinetic studies in three species, and it is the active component of a drug candidate which has progressed to phase 2 clinical studies.

  DOI：

  10.1021/jm050670l
• 作为产物：
  描述：

  1-(3-氨基丙基)吡咯烷 在 palladium on activated charcoal 吡啶 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、358.53 kPa 条件下， 反应 4.0h， 生成 2-methyl-N⁴-[3-(1-pyrrolidinyl)propyl]-1,4-benzenediamine
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Benzophenones Leading to the Discovery of a Potent, Next Generation HIV Nonnucleoside Reverse Transcriptase Inhibitor

  摘要：

  Despite the progress of the past two decades, there is still considerable need for safe, efficacious drugs that target human immunodeficiency virus (HIV). This is particularly true for the growing number of patients infected with virus resistant to currently approved HIV drugs. Our high throughput screening effort identified a benzophenone template as a potential nonnucleoside reverse transcriptase inhibitor (NNRTI). This manuscript describes our extensive exploration of the benzophenone structure-activity relationships, which culminated in the identification of several compounds with very potent inhibition of both wild type and clinically relevant NNRTI-resistant mutant strains of HIV. These potent inhibitors include 70h (GW678248), which has in vitro antiviral assay IC50 values of 0.5 nM against wild-type HIV, 1 nM against the K103N mutant associated with clinical resistance to efavirenz, and 0.7 nM against the Y181C mutant associated with clinical resistance to nevirapine. Compound 70h has also demonstrated relatively low clearance in intravenous pharmacokinetic studies in three species, and it is the active component of a drug candidate which has progressed to phase 2 clinical studies.

  DOI：

  10.1021/jm050670l

文献信息

• Ortho-and/or meta-substituted N-alkylamino secondary para-phenylenediamine, composition for dyeing keratin fibers containing such a para-phenylenediamine, processes using this composition and uses thereof
  申请人：Sabelle Stephane

  公开号：US20060026773A1

  公开（公告）日：2006-02-09

  Novel ortho and/or meta-substituted N-alkylamino secondary para-phenylenediamine compounds, a composition for dyeing keratin fibers, for example, human keratin fibers, such as hair, comprising, in a medium that is suitable for dyeing, at least one ortho- and/or meta-substituted N-alkylamino secondary para-phenylenediamine, a process for dyeing keratin fibers comprising applying the composition, uses of the composition, and a dyeing “kit” comprising the composition.

  新型的邻位和/或间位取代的N-烷基氨基次对苯二胺化合物，一种用于染色角蛋白纤维的组合物，例如人类角蛋白纤维，如头发，包括至少一种适用于染色的邻位和/或间位取代的N-烷基氨基次对苯二胺，在适合染色的介质中，一种染色角蛋白纤维的方法包括应用该组合物，该组合物的用途，以及包括该组合物的染色“套件”。
• Para-phénylénediamine secondaire n-alkylaminée ortho- et/ou méta-substituée, composition de teinture des fibres kératiniques contenant une telle paraphénylènediamine, procédés mettant en oeuvre cette composition et utilisations
  申请人：L'OREAL

  公开号：EP1568686A1

  公开（公告）日：2005-08-31

  La présente demande concerne de nouvelles para-phénylènediamines secondaires N-alkylaminées ortho et/ou méta-substituées, une composition pour la teinture des fibres kératiniques, et en particulier les fibres kératiniques humaines telles que les cheveux, contenant, dans un milieu approprié pour la teinture, au moins une para-phénylènediamine secondaire N-alkylaminée ortho et/ou méta-substituée, un procédé de teinture des fibres kératiniques qui consiste à appliquer cette composition ainsi que les utilisations de cette composition en particulier sous la forme d'un "kit" de teinture.

  本申请涉及新的正代和/或偏代 N-烷基氨基仲对苯二胺，一种用于染色角蛋白纤维，特别是人类角蛋白纤维（如头发）的组合物，该组合物在适于染色的介质中含有至少一种正代和/或偏代 N-烷基氨基仲对苯二胺、至少一种正代和/或偏代 N-烷基胺仲基对苯二胺的组合物，一种使用这种组合物对角蛋白纤维进行染色的工艺，以及这种组合物的用途，尤其是以染色套件的形式使用。
• US7273863B1
  申请人：——

  公开号：US7273863B1

  公开（公告）日：2007-09-25