2-(hydroxy)-N-[2-(1-phenyl-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl)-ethyl]acetamide | 1363375-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(hydroxy)-N-[2-(1-phenyl-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl)-ethyl]acetamide
• 英文别名: 2-(hydroxy)-N-[2-(1-phenyl-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl)ethyl]acetamide；2-hydroxy-N-[2-[2-methyl-5-(4-methylsulfonylphenyl)-1-phenylpyrrol-3-yl]ethyl]acetamide
• CAS: 1363375-32-9
• 化学式: C₂₂H₂₄N₂O₄S
• 分子量: 412.51
• InChiKey: IHRPAYDTBTVHQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(acetoxy)-N-[2-(1-phenyl-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl)-ethyl]acetamide 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到2-(hydroxy)-N-[2-(1-phenyl-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl)-ethyl]acetamide
  参考文献：
  名称：

  1,5-Diaryl-2-alkylpyrrole-3-Substituted Nitro Esters, Selective COX-2 Inhibitors and Nitric Oxide Donors

  摘要：

  提供的是1,5-二芳基-2-烷基吡咯-3-取代硝基酯，其分子式为(I)。这类化合物是强效且选择性的COX-2抑制剂，能够以在浓度上足以抵消由于选择性COX-2抑制引起的副作用的NO释放，而不会引起低血压效应。公式(I)包括的化合物中，基团R'和R"为：—H，—F，—Cl，—Br，—CH3，—CF3，—OCH3，—SCH3，R1为甲基，乙基，三氟甲基，羟甲基，甲氧甲基，且吡咯环上-3位的取代基为链状，其中X、Y、Z、W和R2分别为：X为羰基或—(CHR3)—基团，Y为氧原子或—NR3—基团，Z为羰基或—(CHR3)—基团，或[—CH(COOH)—]基团，或—(NR3)—基团，W为用一或两个(—O—NO2)基团取代的脂肪链，R2为：—H，—OH，—OCH3，或—NHR3。R3为：—H，—CH3，—CH2CH3，[—CH2(CH3)2]。R′″为甲基磺酰基或磺酰胺基。还提供了用于制备和使用此类化合物的药物配方和方法。

  公开号：

  US20130165494A1

文献信息

• 1,5-Diary1-2-alkylpyrrole-3-substituted nitro esters, selective COX-2 inhibitors and nitric oxide donors
  申请人：Giordani Antonio

  公开号：US09162979B2

  公开（公告）日：2015-10-20

  1,5-diaryl-2-alkylpyrrole-3-substituted nitro esters, of Formula (I) are provided. Such compounds are potent and selective COX-2 inhibitors which are able to release NO in concentrations that make it possible to counteract the side effects due to selective COX-2 inhibition, without giving rise to hypotensive effects. Formula (I) includes compounds wherein the groups R′ and R″ are: —H, —F, —Cl, —Br, —CH3, —CF3, —OCH3, —SCH3, R1 is methyl, ethyl, trifluoromethyl, hydroxymethyl, methoxymethyl and the substituent in position −3 of the pyrrole ring is a chain, where the groups X, Y, Z, W and R2 are: X is a carbonyl or a group —(CHR3)—, Y is an oxygen atom or the group —NR3— and Z is a carbonyl or a group —(CHR3)—, or a [—CH(COOH)—] group, or a group —(NR3)—, W is an aliphatic chain substituted with one or two (—O—NO2) groups, R2 is: —H, —OH, —OCH3, or —NHR3. R3 is: —H, —CH3, —CH2CH3, [—CH2(CH3)2]. R′″ is methylsulphonyl or sulphonamido. Pharmaceutical formulations and methods of making an using such formulations are also provided.

  提供了化学式(I)的1,5-二芳基-2-烷基吡咯-3-取代硝酸酯化合物。这些化合物是有效且选择性的COX-2抑制剂，能够释放NO以抵消选择性COX-2抑制引起的副作用，而不会引起低血压作用。化学式(I)包括以下基团：R′和R″为：—H，—F，—Cl，—Br，—CH3，—CF3，—OCH3，—SCH3，R1为甲基，乙基，三氟甲基，羟甲基，甲氧甲基，吡咯环的-3位取代基是链状，其中基团X，Y，Z，W和R2为：X为羰基或—(CHR3)—基团，Y为氧原子或—NR3—基团，Z为羰基或—(CHR3)—基团，或[—CH(COOH)—]基团，或—(NR3)—基团，W为被一个或两个(—O—NO2)基团取代的脂肪链，R2为：—H，—OH，—OCH3或—NHR3。R3为：—H，—CH3，—CH2CH3，[—CH2(CH3)2]。R′″为甲磺酰基或磺酰胺基。还提供了制药配方和使用这种配方的方法。
• [EN] 1,5-DIARYL-2-ALKYLPYRROLE-3-SUBSTITUTED NITRO ESTERS, SELECTIVE COX-2 INHIBITORS AND NITRIC OXIDE DONORS<br/>[FR] NITROESTERS DE L,5-DIARYL-2-ALKYLPYRROLE 3-SUBSTITUÉS, INHIBITEURS SÉLECTIFS DE COX-2 ET DONNEURS D'OXYDE NITRIQUE
  申请人：ROTTAPHARM SPA

  公开号：WO2012032479A8

  公开（公告）日：2012-07-12
• 1,5-DIARYL-2-ALKYLPYRROLE-3-SUBSTITUTED NITRO ESTERS, SELECTIVE COX-2 INHIBITORS AND NITRIC OXIDE DONORS
  申请人：Rottapharm Biotech S.r.l.

  公开号：EP2614050B1

  公开（公告）日：2016-01-20
• US9162979B2
  申请人：——

  公开号：US9162979B2

  公开（公告）日：2015-10-20
• [EN] L,5-DIARYL-2-ALKVLPVRROLE-3-SUBSTITUTED NITRO ESTERS, SELECTIVE COX-2 INHIBITORS AND NITRIC OXIDE DONORS<br/>[FR] NITROESTERS DE L,5-DIARYL-2-ALKYLPYRROLE 3-SUBSTITUÉS, INHIBITEURS SÉLECTIFS DE COX-2 ET DONNEURS D'OXYDE NITRIQUE
  申请人：ROTTAPHARM SPA

  公开号：WO2012032479A1

  公开（公告）日：2012-03-15

  The present invention relates to l,5-diaryl-2-alkylpyrrole-3-substituted nitro esters, of formula (I), which are potent and selective COX-2 inhibitors able to release NO in concentrations that make it possible to counteract the side effects due to selective COX-2 inhibition, without giving rise to hypotensive effects. (I). Where the groups R' and R" are: -H, -F, -CI, -Br, -CH3, -CF3, -OCH3, -SCH3, R1 is methyl, ethyl, trifluoromethyl, hydroxymethyl, methoxymethyl and the substituent in position -3 of the pyrrole ring is a chain, where the groups X, Y, Z, W and R2 are: X is a carbonyl or a group -(CHR3)-, Y is an oxygen atom or the group -NR3- and Z is a carbonyl or a group - (CHR3)-, or a [-CH(COOH)-] group, or a group -(NR3)-, W is an aliphatic chain substituted with one or two (-O-NO2) groups, R2 is: -H, -OH, -OCH3, or -NHR3. R3 is: -H, -CH3, -CH2CH3, [-CH2(CH3)2]. R'" is methylsulphonyl or sulphonamido. The purpose of the invention includes: preparation of the compounds of formula (I), the respective pharmaceutical formulations and use thereof for treating acute and chronic pain, for treating inflammatory disorders and for drug treatment of some forms of tumours.