N-(5-trifluoromethyl-2-pyridinyl)ethanesulfonamide | 141284-82-4

• 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
• 英文名称: N-(5-trifluoromethyl-2-pyridinyl)ethanesulfonamide
• 英文别名: N-(5-trifluoromethyl-2-pyridyl)ethanesulfonamide；N-[5-(trifluoromethyl)pyridin-2-yl]ethanesulfonamide
• CAS: 141284-82-4
• 化学式: C₈H₉F₃N₂O₂S
• 分子量: 254.233
• InChiKey: BJVOLYZUDVJXFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 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

• 作为反应物：
  描述：

  N-(5-trifluoromethyl-2-pyridinyl)ethanesulfonamide 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 Ethanesulfonic acid (3-nitro-5-trifluoromethyl-pyridin-2-yl)-amide
  参考文献：
  名称：

  新型N-（2-磺酰基氨基-5-三氟甲基-3-吡啶基）羧酰胺衍生物作为磷脂酶A2抑制剂的合成及其抗胰腺炎活性。

  摘要：

  已经制备了新的N-（2-磺酰基氨基-5-三氟甲基-3-吡啶基）羧酰胺衍生物，并将其评估为磷脂酶A2（PLA2）抑制剂。在这些化合物中，将IS-741（1j的钠盐）对大鼠通过闭合十二指肠环法诱发的急性出血性胰腺炎显示出最高和最稳定的治疗效果，作为进一步开发的候选药物。

  DOI：

  10.1248/cpb.43.1696
• 作为产物：
  描述：

  2-氯-5-三氟甲基吡啶 生成 N-(5-trifluoromethyl-2-pyridinyl)ethanesulfonamide
  参考文献：
  名称：

  Chem. Pharm. Bull. 1995, 43, 1696-1700

  摘要：

  DOI：

文献信息

• 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。
• Diaminotrifluoromethylpyridine derivatives and phospholipase A.sub.2
  申请人：Ishihara Sangyo Kaisha Ltd.

  公开号：US05229403A1

  公开（公告）日：1993-07-20

  A diaminotrifluoromethylpyridine derivative of the formula (I) or its salt: ##STR1## wherein X is --CW.sup.1 R.sup.1, --COCOR.sup.2, --CW.sup.1 NHCOR.sup.2, --C(.dbd.W.sup.1 (W.sup.2 W.sup.3 or --CW.sup.1 N(R.sup.4)R.sup.5, and Y is alkyl, --CW.sup.3 R.sup.6, --COCOR.sup.7, --NHCOR.sup.7, --C(.dbd.W.sup.3)W.sup.4 R.sup.8, --(NH).sub.m SO.sub.2 R.sup.9, --(NH).sub.m SO.sub.2 OR.sup.10 or --(NH).sub.m SO.sub.2 N R.sup.11)R.sup.12, wherein each of R.sup.1, R.sup.6 and R.sup.9, which are independent from one another, is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted or a polycyclic heterocycle group which may be substituted, each of R.sup.2 and R.sup.7, which are independent from each other, is alkyl which may be substituted, alkoxy which may be substituted, phenyl which may be substituted or phenoxy which may be substituted, each of R.sup.3, R.sup.8 and R.sup.10, which are independent from one another, is alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, cycloalkyl which may be substituted, phenyl which may be substituted or benzyl which may be substituted, each of R.sup.4, R.sup.5, R.sup.11 and R.sup.12, which are independent from one another, is alkyl which may be substituted, each of W.sup.1, W.sup.2, W.sup.3 and W.sup.4, which are independent from one another, is an oxygen atom or a sulfur atom, and m is 0 or 1, provided that a combination wherein one of X and Y is --COCF.sub.2 X.sup.1 wherein X.sup.1 is a hydrogen atom, a halogen atom, alkyl or haloalkyl, and the other is --COCF.sub.2 X.sup.2 wherein X.sub.2 is a hydrogen atom, a halogen atom, alkyl, haloalkyl or alkylcarbonyl, or --COOX.sup.3 wherein X.sup.3 is alkyl which may be substituted or phenyl which may be substituted, is excluded.

  化合物的名称为一种二氟甲基吡啶二胺衍生物的盐，其化学式为（I）：##STR1## 其中X为--CW.sup.1 R.sup.1，--COCOR.sup.2，--CW.sup.1 NHCOR.sup.2，--C(.dbd.W.sup.1(W.sup.2W.sup.3或--CW.sup.1 N(R.sup.4)R.sup.5，Y为烷基，--CW.sup.3 R.sup.6，--COCOR.sup.7，--NHCOR.sup.7，--C(.dbd.W.sup.3)W.sup.4 R.sup.8，--(NH).sub.m SO.sub.2 R.sup.9，--(NH).sub.m SO.sub.2 OR.sup.10或--(NH).sub.m SO.sub.2 NR.sup.11)R.sup.12，其中每个独立的R.sup.1，R.sup.6和R.sup.9是链烃基，可以被取代的单环烃基，可以被取代的多环烃基，可以被取代的单环杂环基或可以被取代的多环杂环基，每个独立的R.sup.2和R.sup.7是可以被取代的烷基，可以被取代的烷氧基，可以被取代的苯基或可以被取代的苯氧基，每个独立的R.sup.3，R.sup.8和R.sup.10是可以被取代的烷基，可以被取代的烯基，可以被取代的炔基，可以被取代的环烷基，可以被取代的苯基或可以被取代的苄基，每个独立的R.sup.4，R.sup.5，R.sup.11和R.sup.12是可以被取代的烷基，每个独立的W.sup.1，W.sup.2，W.sup.3和W.sup.4是氧原子或硫原子，m为0或1，但其中X和Y之一为--COCF.sub.2X.sup.1，其中X.sup.1为氢原子，卤原子，烷基或卤代烷基，另一个为--COCF.sub.2X.sup.2，其中X.sub.2为氢原子，卤原子，烷基，卤代烷基或烷基羰基，或--COOX.sup.3，其中X.sup.3是可以被取代的烷基或可以被取代的苯基。
• Diaminotrifluoromethylpyridine derivatives, process for their production
  申请人：Ishihara Sangyo Kaisha Ltd.

  公开号：US05492908A1

  公开（公告）日：1996-02-20

  A method of treating rheumatoid arthritis using a diaminotrifluoromethylpyridine derivative of the formula (I) or its salt: ##STR1## wherein X is --CW.sup.1 R.sup.1, --COCOR.sup.2, --CW.sup.1 NHCOR.sup.2, --C(.dbd.W.sup.1)W.sup.2 R.sup.3 or --CW.sup.1 N(R.sup.4)R.sup.5, and Y is alkyl, --CW.sup.3 R.sup.6, --COCOR.sup.7, --NHCOR.sup.7, --C(.dbd.W.sup.3)W.sup.4 R.sup.8, --(NH).sub.m SO.sub.2 R.sup.9, --(NH).sub.m SO.sub.2 OR.sup.10 or --(NH).sub.m SO.sub.2 N(R.sup.11)R.sup.12, wherein each of R.sup.1, R.sup.6 and R.sup.9, which are independent from one another, is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted or a polycyclic heterocycle group which may be substituted as further defined herein.

  使用公式（I）或其盐的二氨基三氟甲基吡啶衍生物治疗类风湿性关节炎的方法： 其中X为--CW1R1，--COCOR2，--CW1NHCOR2，--C(.dbd.W1)W2R3或--CW1N(R4)R5，Y为烷基，--CW3R6，--COCOR7，--NHCOR7，--C(.dbd.W3)W4R8，--(NH)mSO2R9，--(NH)mSO2OR10或--(NH)mSO2N(R11)R12，其中R1，R6和R9分别是独立的链烃基，可以被取代的单环烃基，可以被取代的多环烃基，可以被取代的单环杂环基或可以被取代的多环杂环基，如此处进一步定义。
• Diaminotrifluoromethylpyridine compounds and phospholipase A.sub.2
  申请人：Ishihara Sangyo Kaisha Ltd.

  公开号：US05260320A1

  公开（公告）日：1993-11-09

  A diaminotrifluoromethylpyridine derivative of the formula (I) or its salt: ##STR1## wherein X is --CW.sup.1 R.sup.1, --COCOR.sup.2, --CW.sup.1 NHCOR.sup.2, --C(.dbd.W.sup.1)W.sup.2 R.sup.3 or --CW.sup.1 N(R.sup.4)R.sup.5, and Y is alkyl, --CW.sup.3 R.sup.6, --COCOR.sup.7, --NHCOR.sup.7, --C(.dbd.W.sup.3)W.sup.4 R.sup.8, --(NH).sub.m SO.sub.2 R.sup.9, --(NH).sub.m SO.sub.2 OR.sup.10 or --(NH).sub.m SO.sub.2 N(R.sup.11)R.sup.12, wherein each of R.sup.1, R.sup.6 and R.sup.9, which are independent from one another, is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted or a polycyclic heterocycle group which may be substituted, each of R.sup.2 and R.sup.7, which are independent from each other, is alkyl which may be substituted, alkoxy which may be substituted, phenyl which may be substituted or phenoxy which may be substituted, each of R.sup.3, R.sup.8 and R.sup.10, which are independent from one another, is alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, cycloalkyl which may be substituted, phenyl which may be substituted or benzyl which may be substituted, each of R.sup.4, R.sup.5, R.sup.11 and R.sup.12, which are independent from one another, is alkyl which may be substituted, each of W.sup.1, W.sup.2, W.sup.3 and W.sup.4, which are independent from one another, is an oxygen atom or a sulfur atom, and m is 0 or 1, provided that a combination wherein one of X and Y is --COCF.sub.2 X.sup.1 wherein X.sup.1 is a hydrogen atom, a halogen atom, alkyl or haloalkyl, and the other is --COCF.sub.2 X.sup.2 wherein X.sup.2 is a hydrogen atom, a halogen atom, alkyl, haloalkyl or alkylcarbonyl, or --COOX.sup.3 wherein X.sup.3 is alkyl which may be substituted or phenyl which may be substituted, is excluded.

  一种公式（I）或其盐的二氨基三氟甲基吡啶衍生物：##STR1## 其中X是--CW.sup.1 R.sup.1，--COCOR.sup.2，--CW.sup.1 NHCOR.sup.2，--C（.dbd.W.sup.1）W.sup.2 R.sup.3或--CW.sup.1 N（R.sup.4）R.sup.5，而Y是烷基，--CW.sup.3 R.sup.6，--COCOR.sup.7，--NHCOR.sup.7，--C（.dbd.W.sup.3）W.sup.4 R.sup.8，--（NH）.sub.m SO.sub.2 R.sup.9，--（NH）.sub.m SO.sub.2 OR.sup.10或--（NH）.sub.m SO.sub.2 N（R.sup.11）R.sup.12，其中R.sup.1，R.sup.6和R.sup.9互相独立，分别是链烃基，可取代的单环烃基，可取代的多环烃基，可取代的单环杂环基或可取代的多环杂环基，R.sup.2和R.sup.7互相独立，分别是可取代的烷基，可取代的烷氧基，可取代的苯基或可取代的苯氧基，R.sup.3，R.sup.8和R.sup.10互相独立，分别是可取代的烷基，可取代的烯基，可取代的炔基，可取代的环烷基，可取代的苯基或可取代的苄基，R.sup.4，R.sup.5，R.sup.11和R.sup.12互相独立，分别是可取代的烷基，W.sup.1，W.sup.2，W.sup.3和W.sup.4互相独立，分别是氧原子或硫原子，m为0或1，但排除其中一个X和Y是--COCF.sub.2X.sup.1，其中X.sup.1是氢原子，卤素原子，烷基或卤代烷基，另一个是--COCF.sub.2X.sup.2，其中X.sup.2是氢原子，卤素原子，烷基，卤代烷基或烷基羰基，或--COOX.sup.3，其中X.sup.3是可取代的烷基或可取代的苯基的组合。
• Diaminotrifluoromethylpyrimidine derivatives, process for their production and phospholipase A2 inhibitor containing them
  申请人：ISHIHARA SANGYO KAISHA, LTD.

  公开号：EP0465913B1

  公开（公告）日：1997-09-10