5-methyl-N-(2-methyl-4-nitrophenyl)isoxazole-4-carboxamide

• 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: 5-methyl-N-(2-methyl-4-nitrophenyl)isoxazole-4-carboxamide
• 英文别名: 5-methyl-N-(2-methyl-4-nitrophenyl)-1,2-oxazole-4-carboxamide
• 化学式: C₁₂H₁₁N₃O₄
• mdl: MFCD09971676
• 分子量: 261.237
• InChiKey: LQTBHXULKJCGFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-N-(2-methyl-4-nitrophenyl)isoxazole-4-carboxamide 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 7.0h， 生成 5-methylisoxazole-4-carboxylic acid {2-methyl-4-[3-(3-(trifluoromethyl)phenyl)ureido]phenyl}amide
  参考文献：
  名称：

  Discovery of 4-arylamido 3-methyl isoxazole derivatives as novel FMS kinase inhibitors

  摘要：

  A series of 4-arylamido 3-methyl isoxazoles were synthesized and evaluated for their antiproliferative activities against the A375P melanoma and U937 hematopoietic cell lines. Most compounds showed selective antiproliferative activity toward the U937 cell line and the activities were better than that of sorafenib, the reference standard. Derivatives were made as amide 5a-b, 6a-o and urea 7a-n, 8a-g with hydrophobic moieties, and one of the most potent inhibitor 6a, 5-methyl-N-(2-methyl-5-(3-(4-methylpiperazin-l-yl)-5-(trifluoromethyl)benzamido)pherwl)isoxazole-4-carboxamide was found to be very potent inhibitor of FMS kinase (GI(50) = 0.016 mu M, IC50 = 9.95 nM) with excellent selectivity profiles and is a promising candidate for further development in therapeutics for cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.031
• 作为产物：
  描述：

  5-甲基异恶唑-4-甲酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 5-methyl-N-(2-methyl-4-nitrophenyl)isoxazole-4-carboxamide
  参考文献：
  名称：

  N-(5-아릴아미도-2-메틸페닐)-5-메틸이소옥사졸-4-카복스아미드 유도체, 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 FMS 키나아제 저해제

  摘要：

  本发明涉及化合物，其用化学式1表示，或其药学上可接受的盐及包含该盐的药学组合物。根据本发明的化合物可表现出FMS激酶抑制活性，可用作与之相关疾病的预防或治疗药学组合物。在上述式中，R和R的定义如规范中所定义。

  公开号：

  KR20160034632A

文献信息

• N-(5-아릴아미도-2-메틸페닐)-5-메틸이소옥사졸-4-카복스아미드 유도체, 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 FMS 키나아제 저해제
  申请人：Industry-University Cooperation Foundation Hanyang University ERICA Campus 한양대학교 에리카산학협력단(120120008551) Corp. No ▼ 131471-0017977BRN ▼134-82-10205

  公开号：KR20160034632A

  公开（公告）日：2016-03-30

  본 발명은 하기 화학식 1로 표시되는 화합물, 또는 이의 약학적으로 허용가능한 염 및 이를 포함하는 약학적 조성물에 관한 것이다. 본 발명에 따른 화합물은 FMS 키나아제 저해 활성을 나타내어 이와 관련된 질환의 예방 또는 치료용 약학적 조성물로 사용될 수 있다. [화학식 1] 상기 식에서, R 및 R의 정의는 명세서에 정의된 바와 같다.

  本发明涉及化合物，其用化学式1表示，或其药学上可接受的盐及包含该盐的药学组合物。根据本发明的化合物可表现出FMS激酶抑制活性，可用作与之相关疾病的预防或治疗药学组合物。在上述式中，R和R的定义如规范中所定义。
• N-(5-ARYLAMIDO-2-METHYLPHENYL)-5-METHYLISOOXAZOLE-4-CARBOXAMIDE DERAVATIVE, PHARMACEUTICAL ACCEPTABLE SALT THEREOF, METHOD FOR PREPARATION THEROF AND FMS KINASE INHIBITOR COMPRISING THE SAME AS ANACTIVE INGREDIENT
  申请人：Industry-University Cooperation Foundation Hanyang University ERICA Campus

  公开号：US20170273947A1

  公开（公告）日：2017-09-28

  The present invention relates to N-(5-arylamido-2-methylphenyl)-5-methylisoquoxazole-4-carboxamide derivative, or a pharmaceutically acceptable salt thereof and a pharmaceutical composition comprising same. The compound according to the present invention exhibits an FMS kinase inhibitory activity and thus can be used as pharmaceutical composition for preventing and treating diseases associated therewith.
• US9789086B1
  申请人：——

  公开号：US9789086B1

  公开（公告）日：2017-10-17
• Discovery of 4-arylamido 3-methyl isoxazole derivatives as novel FMS kinase inhibitors
  作者：Daseul Im、Kyungjin Jung、Songyi Yang、Waqar Aman、Jung-Mi Hah

  DOI：10.1016/j.ejmech.2015.08.031

  日期：2015.9

  A series of 4-arylamido 3-methyl isoxazoles were synthesized and evaluated for their antiproliferative activities against the A375P melanoma and U937 hematopoietic cell lines. Most compounds showed selective antiproliferative activity toward the U937 cell line and the activities were better than that of sorafenib, the reference standard. Derivatives were made as amide 5a-b, 6a-o and urea 7a-n, 8a-g with hydrophobic moieties, and one of the most potent inhibitor 6a, 5-methyl-N-(2-methyl-5-(3-(4-methylpiperazin-l-yl)-5-(trifluoromethyl)benzamido)pherwl)isoxazole-4-carboxamide was found to be very potent inhibitor of FMS kinase (GI(50) = 0.016 mu M, IC50 = 9.95 nM) with excellent selectivity profiles and is a promising candidate for further development in therapeutics for cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.