5-氨基-6-甲基-2-吡啶磺酰胺 | 329947-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-氨基-6-甲基-2-吡啶磺酰胺
• 英文名称: 5-amino-6-methyl-2-pyridinesulfonamide
• 英文别名: 5-amino-6-methylpyridine-2-sulfonamide
• CAS: 329947-26-4
• 化学式: C₆H₉N₃O₂S
• mdl: MFCD09031570
• 分子量: 187.222
• InChiKey: PCDZAAVCRAOGRP-UHFFFAOYSA-N

物化性质

• 沸点：
  458.6±55.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氨基-6-甲基-2-吡啶磺酰胺 、 [4-chloro-2-(3-chloro-5-cyanobenzoyl)phenoxy]acetyl chloride 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以0.033 g的产率得到2-[4-chloro-2-(3-chloro-5-cyano-benzoyl)phenoxy]-N-(2-methyl-6-sulfamoyl-3-pyridyl)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：

  6-氯-2-甲基-3-硝基吡啶 在 palladium on activated charcoal 盐酸 、 氢气 、 氯 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 8.75h， 生成 5-氨基-6-甲基-2-吡啶磺酰胺
  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

• [EN] BENZOPHENONES AS INHIBITORS OF REVERSE TRANSCRIPTASE<br/>[FR] BENZOPHENONES AGISSANT COMME INHIBITEURS DE LA TRANSCRIPTASE INVERSE
  申请人：GLAXO GROUP LTD

  公开号：WO2001017982A1

  公开（公告）日：2001-03-15

  The present invention includes benzophenone compounds (I) which are useful in the treatment of HIV infections.

  本发明包括苯甲酮化合物（I），其在治疗HIV感染方面具有用处。
• CHEMICAL COMPOUNDS
  申请人：Jones Lyn Howard

  公开号：US20090264425A1

  公开（公告）日：2009-10-22

  This invention relates to biaryl ether derivatives of formula (I) wherein R 1 , R 3 , R 4 , X, W, Y and m are defined in the description, and to compositions containing them and the uses of such derivatives. The compounds of the present invention bind to the enzyme reverse transcriptase and are modulators, especially inhibitors thereof.

  本发明涉及公式（I）的二芳基醚衍生物，其中R1、R3、R4、X、W、Y和m在说明中定义，并涉及含有它们的组合物以及这些衍生物的用途。本发明的化合物与酶逆转录酶结合，并且是其调节剂，特别是抑制剂。
• Benzophenones as inhibitors of reverse transcriptase
  申请人：GLAXO GROUP LIMITED

  公开号：EP1710238A1

  公开（公告）日：2006-10-11

  The present invention includes benzophenone compounds (I) which are useful in the treatment of HIV infections.

  本发明包括二苯甲酮化合物 (I)，它们可用于 治疗艾滋病病毒感染。
• BENZOPHENONES AS INHIBITORS OF REVERSE TRANSCRIPTASE
  申请人：GLAXO GROUP LIMITED

  公开号：EP1208091B1

  公开（公告）日：2006-05-03
• NONNUCLEOSIDE INHIBITORS OF HIV-1 REVERSE TRANSCRIPTASE
  申请人：Pfizer Limited

  公开号：EP1831157A2

  公开（公告）日：2007-09-12