ethyl o-mesitylsulfonylacetohydroxamic acid

• 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: ethyl o-mesitylsulfonylacetohydroxamic acid
• 英文别名: N-hydroxy-2-(2,4,6-trimethylphenyl)sulfonylbutanamide
• 化学式: C₁₃H₁₉NO₄S
• 分子量: 285.364
• InChiKey: GCAZPZBNAMEHGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲氧基吡啶 、 ethyl o-mesitylsulfonylacetohydroxamic acid 在 高氯酸 作用下， 以 1,4-二氧六环 、 水 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-aminopyridinium 2,4,6-trimethylbenzenesulfonate
  参考文献：
  名称：

  Discovery of novel pyrazolo[1,5-a]pyridine-based EP1 receptor antagonists by scaffold hopping: Design, synthesis, and structure-activity relationships

  摘要：

  A scaffold-hopping strategy towards a new pyrazolo[1,5-a]pyridine based core using molecular hybridization of two structurally distinct EP1 antagonists, followed by structure-activity relationship guided optimization, resulted in the identification of potent EP1 antagonists exemplified by 4c, 4f, and 4j, which were shown to reduce pathological intravesical pressure in rats when administered at 1 mg/kg iv. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2017.07.055
• 作为试剂：
  描述：

  4-三氟甲基吡啶 、 苯丙炔酸甲酯 在 高氯酸 、 ethyl o-mesitylsulfonylacetohydroxamic acid 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以92%的产率得到methyl 2-phenyl-5-(trifluoromethyl)pyrazolo[1,5-a]pyridine-3-carboxylate
  参考文献：
  名称：

  新型吡唑并[1,5-a]吡啶类作为口服活性EP1受体拮抗剂：合成，结构-活性关系研究和生物学评估。

  摘要：

  设计，合成和评价新型吡唑并[1,5-a]吡啶衍生物作为口服活性EP1拮抗剂，用于治疗膀胱过度活动症。匹配的分子对分析（MMPA）允许设计一系列新的吡唑并[1,5-a]吡啶衍生物4-6。进行了4-6的结构-活性关系（SAR）研究，鉴定了纳摩尔水平的EP1拮抗剂4c，在17-苯基trinor前列腺素E2诱导的膀胱收缩模型中，通过十二指肠内（id）给药显示出良好的药理作用在大鼠中。

  DOI：

  10.1016/j.bmc.2017.03.003

文献信息

• Substituted triazolopyridine compounds
  申请人：——

  公开号：US20030207911A1

  公开（公告）日：2003-11-06

  A compound of formula 1 wherein R 1 is —NR′R″, wherein R′ and R″ are independently selected from the group consisting of lower alkyl, —(CH 2 ) n —C(O)NR a R b , —(CH 2 ) n -heteroaryl, —(CH 2 ) n -aryl, —(CH 2 ) n —CN, —(CH 2 ) n —O-lower alkyl or —(CH 2 ) n -cycloalkyl, or R′ and R″ form together with the N-atom a five or six-membered non- aromatic ring, containing no or one additional heteroatom selected from the group consiting of O and S, and said ring being unsubstituted or substituted by one or two substituents, selected from the group consisting of lower alkyl, —C(O)NR a R b and —(CH 2 ) n —O-lower alkyl, and R a R b are independently from each other hydrogen or lower alkyl; R 2 is aryl or heteroaryl, unsubstituted or substituted by lower alkyl or halogen; and n is 0, 1, 2 or 3; or a pharmaceutically acceptable salt thereof. Compounds of formula I are useful in the treatment of disease associated with the adenosine A2 receptor.

  式1的化合物，其中R1为—NR′R″，其中R′和R″分别选自下列基团：较低烷基，—(CH2)n—C(O)NRaRb，—(CH2)n-杂环芳基，—(CH2)n-芳基，—(CH2)n—CN，—(CH2)n—O-较低烷基或—(CH2)n-环烷基，或者R′和R″与N原子一起形成一个不含或含有O和S中选择的一个额外杂原子的五元或六元非芳香环，该环未取代或取代一个或两个取代基，所选自较低烷基，—C(O)NRaRb和—(CH2)n—O-较低烷基的基团，且RaRb各自独立为氢或较低烷基；R2为芳基或杂环芳基，未取代或取代为较低烷基或卤素；n为0、1、2或3；或其药学上可接受的盐。式I的化合物在治疗与腺苷A2受体相关的疾病中很有用。
• 8-AMINO- 1,2,4]TRIAZOLO 1,5-A]PYRIDINE-6-CARBOXYLIC ACID AMIDE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1435952A1

  公开（公告）日：2004-07-14
• US6689790B2
  申请人：——

  公开号：US6689790B2

  公开（公告）日：2004-02-10
• [EN] 8-AMINO-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE-6-CARBOXYLIC ACID AMIDE<br/>[FR] AMIDE D'ACIDE 8-AMINO-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE-6-CARBOXYLIQUE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003030904A1

  公开（公告）日：2003-04-17

  The invention relates to compounds of formula (I), wherein R1 is -NR'R', wherein R' and R' are independently from each other lower alkyl, -(CH¿2?)n-C(O)NR?aRb¿, -(CH¿2?)n-heteroaryl, -(CH2)n-aryl, -(CH2)n-CN, -(CH2)n-O-lower alkyl or -(CH2)n-cycloalkyl, or R'and R' form together with the N-atom a five or six-membered none aromatic ring, which may contain one additional O or S heteroatom, and whose rings may be unsubstituted or substituted by one or two substituents, selected from the group consisting of lower alkyl, -C(O)NR?aRb¿ or -(CH¿2?)n-O-lower alkyl and R?aRb¿ are independently from each other hydrogen or lower alkyl; R2 is aryl or heteroaryl, unsubstituted or substituted ba lower alkyl or halogen; n is 0, 1, 2 or 3; and to their pharmaceutically acceptable salts. The compounds may be used in the treatment of diseases, associated with the adenosime A2 receptor.
• Discovery of novel pyrazolo[1,5-a]pyridine-based EP1 receptor antagonists by scaffold hopping: Design, synthesis, and structure-activity relationships
  作者：Yosuke Nishigaya、Kentaro Umei、Yoshifumi Saito、Hiroyuki Watanabe、Tatsuhiro Kondo、Atsushi Kondo、Naohiro Kawamura、Kazuya Tatani、Yasushi Kohno、Nobuyuki Tanaka、Shigeki Seto

  DOI：10.1016/j.bmcl.2017.07.055

  日期：2017.9

  A scaffold-hopping strategy towards a new pyrazolo[1,5-a]pyridine based core using molecular hybridization of two structurally distinct EP1 antagonists, followed by structure-activity relationship guided optimization, resulted in the identification of potent EP1 antagonists exemplified by 4c, 4f, and 4j, which were shown to reduce pathological intravesical pressure in rats when administered at 1 mg/kg iv. (C) 2017 Published by Elsevier Ltd.