N-(6-chloro-5-trifluoromethyl-2-pyridinyl)ethanesulfonamide | 163238-02-6

• 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
• 英文名称: N-(6-chloro-5-trifluoromethyl-2-pyridinyl)ethanesulfonamide
• 英文别名: N-[5-(Trifluoromethyl)-6-chloro-2-pyridyl]ethanesulfonamide；N-[6-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanesulfonamide
• CAS: 163238-02-6
• 化学式: C₈H₈ClF₃N₂O₂S
• 分子量: 288.678
• InChiKey: SEOIPOFKXOUYFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,6-二氯-3-(三氟甲基)吡啶 、 乙基磺酰胺 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以56%的产率得到N-(6-chloro-5-trifluoromethyl-2-pyridinyl)ethanesulfonamide
  参考文献：
  名称：

  Synthesis of N-(Trifluoromethyl-2-pyridinyl)arenesulfonamides as an Inhibitor of Secretory Phospholipase A2

  摘要：

  一系列N-(三氟甲基-2-吡啶基)烷基和芳基磺酰胺2—5通过2-氯(三氟甲基)吡啶6与烷基和芳基磺酰胺7的取代反应合成。测定了它们对猪胰腺分泌磷脂酶A2的抑制活性，发现类似物N-[4,5-双(三氟甲基)-2-吡啶基]-4-三氟甲基苯磺酰胺4i具有最高的抑制活性，IC50值为0.58 mM。

  DOI：

  10.1248/cpb.59.783

文献信息

• Process for preparing 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamides
  申请人：Maligres E. Peter

  公开号：US20050014780A1

  公开（公告）日：2005-01-20

  The preparation of 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamides is disclosed. A 5-halo-8-hydroxy-1,6-napthyridine-7-carboxylic acid or acid ester in which the hydroxy is derivatized with a protecting group is reacted with a sulfonamide (e.g., an alkanesulfonamide, N-alkyl alkanesulfonamide, or alkanesultam) in the presence of a copper promoter and a chelating agent, followed by deprotection of the hydroxy group, and then coupling with an amine to obtain the 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamide. Alternatively, the hydroxy-protected 5-halo-8-hydroxy-1,6-napthyridine-7-carboxylic acid (or ester) is first coupled with an amine, the resulting carboxamide reacted with a sulfonamide followed by deprotection of the hydroxy group to obtain the 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamide. The 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamides are inhibitors of HIV integrase and are useful for treating HIV infection, preventing HIV infection, delaying the onset of AIDS, and treating AIDS.

  本文公开了制备5-磺酰胺基-8-羟基-1,6-萘啶-7-羧酸酰胺的方法。首先将5-卤代-8-羟基-1,6-萘啶-7-羧酸或酸酯与保护羟基的衍生物反应，加入磺酰胺（例如，烷基磺酰胺，N-烷基磺酰胺或烷基磺酰胺）和铜催化剂以及螯合剂，去除保护羟基，然后与胺偶联，得到5-磺酰胺基-8-羟基-1,6-萘啶-7-羧酸酰胺。或者，先将保护羟基的5-卤代-8-羟基-1,6-萘啶-7-羧酸（或酯）与胺偶联，然后将产生的羧酰胺与磺酰胺反应，去除保护羟基，得到5-磺酰胺基-8-羟基-1,6-萘啶-7-羧酸酰胺。5-磺酰胺基-8-羟基-1,6-萘啶-7-羧酸酰胺是HIV整合酶的抑制剂，可用于治疗HIV感染，预防HIV感染，延缓艾滋病的发作和治疗艾滋病。
• PROCESS FOR PREPARING 5-SULFONAMIDO-8-HYDROXY-1, 6-NAPHTHYRIDINE-7-CARBOXAMIDES
  申请人：Merck & Co., Inc.

  公开号：EP1427726A1

  公开（公告）日：2004-06-16
• [EN] PROCESS FOR PREPARING 5-SULFONAMIDO-8-HYDROXY-1, 6-NAPHTHYRIDINE-7-CARBOXAMIDES<br/>[FR] PROCEDE DE PREPARATION DE 5-SULFONAMIDO-8-HYDROXY-1, 6-NAPHTYRIDINE-7-CARBOXAMIDES
  申请人：MERCK & CO INC

  公开号：WO2003016309A1

  公开（公告）日：2003-02-27

  The preparation of 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamides is disclosed. A 5-halo-8-hydroxy-1,6-napthyridine-7-carboxylic acid or acid ester in which the hydroxy is derivatized with a protecting group is reacted with a sulfonamide (e.g., an alkanesulfonamide, N-alkyl alkanesulfonamide, or alkanesultam) in the presence of a copper promoter and a chelating agent, followed by deprotection of the hydroxy group, and then coupling with an amine to obtain the 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamide. Alternatively, the hydroxy-protected 5-halo-8-hydroxy-1,6-napthyridine-7-carboxylic acid (or ester) is first coupled with an amine, the resulting carboxamide reacted with a sulfonamide followed by deprotection of the hydroxy group to obtain the 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamide. The 5-sulfonamido-8-hydroxy-1,6-naphthyridine-7-carboxamides are inhibitors of HIV integrase and are useful for treating HIV infection, preventing HIV infection, delaying the onset of AIDS, and treating AIDS.
• Synthesis of N-(Trifluoromethyl-2-pyridinyl)arenesulfonamides as an Inhibitor of Secretory Phospholipase A2
  作者：Hitoshi Nakayama、Yuka Morita、Hirohiko Kimura、Keiichi Ishihara、Satoshi Akiba、Jun'ichi Uenishi

  DOI：10.1248/cpb.59.783

  日期：——

  A series of N-(trifluoromethyl-2-pyridinyl)alkane- and arenesulfonamides 2—5 have been synthesized by the substitution reaction of 2-chloro(trifluoromethyl)pyridines 6 with alkane- and arenesulfonamides 7. Their inhibitory activities against secretory phospholipase A2 of porcine pancreas were examined and the analog N-[4,5-bis(trifluoromethyl)-2-pyridinyl]-4-trifluoromethylbenzenesulfonamide 4i was shown to have the highest inhibitory activity, with an IC50 value of 0.58 mM.

  一系列N-(三氟甲基-2-吡啶基)烷基和芳基磺酰胺2—5通过2-氯(三氟甲基)吡啶6与烷基和芳基磺酰胺7的取代反应合成。测定了它们对猪胰腺分泌磷脂酶A2的抑制活性，发现类似物N-[4,5-双(三氟甲基)-2-吡啶基]-4-三氟甲基苯磺酰胺4i具有最高的抑制活性，IC50值为0.58 mM。