1-Benzyl-4-[N-methyl-N-(3-nitro-6-chloro-2-pyridinyl)amino]piperidine | 179557-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Benzyl-4-[N-methyl-N-(3-nitro-6-chloro-2-pyridinyl)amino]piperidine
• 英文别名: N-(1-benzylpiperidin-4-yl)-6-chloro-N-methyl-3-nitropyridin-2-amine
• CAS: 179557-85-8
• 化学式: C₁₈H₂₁ClN₄O₂
• 分子量: 360.843
• InChiKey: XWDZRTKSGQXFCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-Benzyl-4-[N-methyl-N-(3-nitro-6-chloro-2-pyridinyl)amino]piperidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-N-(1-benzylpiperidin-4-yl)-6-chloro-2-N-methylpyridine-2,3-diamine
  参考文献：
  名称：

  Targeting Delavirdine/Atevirdine Resistant HIV-1:  Identification of (Alkylamino)piperidine-Containing Bis(heteroaryl)piperazines as Broad Spectrum HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  A novel class of bis(heteroaryl)piperazine (BHAP) analogs which possesses the ability to inhibit NNRTI (non-nucleoside reverse transcriptase inhibitor) resistant recombinant HIV-1 reverse transcriptase (RT) and NNRTI resistant variants of HIV-1 has been identified via targeted screening. Further investigation of the structure-activity relationships of close congeners of these novel (alkylamino)piperidine BHAPs (AAP-BHPSs) led to the synthesis of several compounds possessing the desired phenotype (e.g., activity against recombinant RTs carrying the Y181C and P236L substitutions). Further structural modifications were required to inhibit metabolism and modulate solubility in order to obtain compounds with the desired biological profile as well as appropriate pharmaceutical properties. The AAP-BHAPs with the most suitable characteristics were compounds 7, 15, and 36.

  DOI：

  10.1021/jm960158n
• 作为产物：
  描述：

  N-苄基哌啶酮 在 4 A molecular sieve 、 sodium cyanoborohydride 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 144.0h， 生成 1-Benzyl-4-[N-methyl-N-(3-nitro-6-chloro-2-pyridinyl)amino]piperidine
  参考文献：
  名称：

  Targeting Delavirdine/Atevirdine Resistant HIV-1:  Identification of (Alkylamino)piperidine-Containing Bis(heteroaryl)piperazines as Broad Spectrum HIV-1 Reverse Transcriptase Inhibitors

  摘要：

  A novel class of bis(heteroaryl)piperazine (BHAP) analogs which possesses the ability to inhibit NNRTI (non-nucleoside reverse transcriptase inhibitor) resistant recombinant HIV-1 reverse transcriptase (RT) and NNRTI resistant variants of HIV-1 has been identified via targeted screening. Further investigation of the structure-activity relationships of close congeners of these novel (alkylamino)piperidine BHAPs (AAP-BHPSs) led to the synthesis of several compounds possessing the desired phenotype (e.g., activity against recombinant RTs carrying the Y181C and P236L substitutions). Further structural modifications were required to inhibit metabolism and modulate solubility in order to obtain compounds with the desired biological profile as well as appropriate pharmaceutical properties. The AAP-BHAPs with the most suitable characteristics were compounds 7, 15, and 36.

  DOI：

  10.1021/jm960158n

文献信息

• Alkyl substituted piperadinyl and piperazinyl anti-AIDS compounds
  申请人：Pharmacia & Upjohn Company

  公开号：US05866589A1

  公开（公告）日：1999-02-02

  Anti-AIDS compounds of formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, and R.sub.7 are as defined in the specification and R.sub.8 is alkyl of substituted alkyl.

  化合物的抗艾滋病公式（I）##STR1##其中R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5、R.sub.6和R.sub.7如规范中定义，R.sub.8是取代烷基的烷基。
• [EN] ALKYL SUBSTITUTED PIPERADINYL AND PIPERAZINYL ANTI-AIDS COMPOUNDS<br/>[FR] COMPOSES DE PIPERADINYLE ET PIPERAZINYLE ANTI-SIDA A SUBSTITUTION ALKYLE
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：WO1996018628A1

  公开（公告）日：1996-06-20

  (EN) Anti-AIDS compounds of formula (I), where the aromatic/heteroaromatic ring is bonded to a carbon atom of the R8 substituent are disclosed as well as specific Anti-AIDS pyridines (V).(FR) L'invention se rapporte à des composés anti-SIDA de la formule (I) dans laquelle le noyau aromatique/hétéroaromatique est lié à un atome de carbone du substituant de R8, ainsi qu'à des pyridines (V) spécifiques anti-SIDA.

  抗艾滋病化合物的公式（I）被揭示，其中芳香/杂环芳香环与R8取代基的一个碳原子结合，以及特定的抗艾滋病吡啶（V）。
• US5866589A
  申请人：——

  公开号：US5866589A

  公开（公告）日：1999-02-02
• Targeting Delavirdine/Atevirdine Resistant HIV-1:  Identification of (Alkylamino)piperidine-Containing Bis(heteroaryl)piperazines as Broad Spectrum HIV-1 Reverse Transcriptase Inhibitors
  作者：Donna L. Romero、Robert A. Olmsted、Toni Jo Poel、Raymond A. Morge、Carolyn Biles、Barbara J. Keiser、Laurice A. Kopta、Jan M. Friis、John D. Hosley、Kevin J. Stefanski、Donn G. Wishka、David B. Evans、Joel Morris、Randy G. Stehle、Satish K. Sharma、Yoshihiko Yagi、Richard L. Voorman、Wade J. Adams、W. Gary Tarpley、Richard C. Thomas

  DOI：10.1021/jm960158n

  日期：1996.1.1

  A novel class of bis(heteroaryl)piperazine (BHAP) analogs which possesses the ability to inhibit NNRTI (non-nucleoside reverse transcriptase inhibitor) resistant recombinant HIV-1 reverse transcriptase (RT) and NNRTI resistant variants of HIV-1 has been identified via targeted screening. Further investigation of the structure-activity relationships of close congeners of these novel (alkylamino)piperidine BHAPs (AAP-BHPSs) led to the synthesis of several compounds possessing the desired phenotype (e.g., activity against recombinant RTs carrying the Y181C and P236L substitutions). Further structural modifications were required to inhibit metabolism and modulate solubility in order to obtain compounds with the desired biological profile as well as appropriate pharmaceutical properties. The AAP-BHAPs with the most suitable characteristics were compounds 7, 15, and 36.