2-(methylthio)-3-nitro-4,5-dihydropyrrole | 74188-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2-(methylthio)-3-nitro-4,5-dihydropyrrole
• 英文别名: 2-methylthio-3-nitro-4,5-dihydropyrrole；2-Methylthio-3-nitro4,5-dihydropyrrole；5-methylsulfanyl-4-nitro-2,3-dihydro-1H-pyrrole
• CAS: 74188-62-8
• 化学式: C₅H₈N₂O₂S
• 分子量: 160.197
• InChiKey: JQZNJWLOUDDZBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  83.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(methylthio)-3-nitro-4,5-dihydropyrrole 、 2-(((5-甲基-1H-咪唑-4-基)甲基)硫代)乙胺 在 水合甲醇 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-3-nitro-4,5-dihydropyrrole (1.4 g, 66%) m.p. 207.5°-208°的产率得到2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-3-nitro-4,5-dihydropyrrole
  参考文献：
  名称：

  1-Benzyl-5-nitro-4-(pyridyl or imidazolyl)

  摘要：

  具有3-硝基和2-杂环基烷基氨基基团的2,3-不饱和含氮杂环化合物。2-位置取代基的烷基团最好被硫或氧所中断。该发明的化合物最好是二氢吡咯或四氢吡啶或嘧啶。该发明的化合物是组胺H.sub.2受体拮抗剂。

  公开号：

  US04324789A1
• 作为产物：
  描述：

  1-nitro-2-(methylthio)-2-aziridinoethene 在 potassium iodide 作用下， 以 丙酮 为溶剂， 以34%的产率得到2-(methylthio)-3-nitro-4,5-dihydropyrrole
  参考文献：
  名称：

  Dipole moment in relation to hydrogen receptor histamine antagonist activity for cimetidine analogs

  摘要：

  The activities of a series of H2 receptor histamine antagonists structurally related to cimetidine (1) have been compared to investigate the effect of replacing the cyanoguanidine moiety by other neutral, dipolar groups. Antagonist activity, as measured in vitro on the histamine-stimulated guinea pig right atrium, was found to be very sensitive to relatively minor structural changes. Differences in H2 antagonist activity are accounted for by dipole moment orientation and lipophilicity and are rationalized in terms of an optimum requirement for alignment of a hydrogen-bonding moiety in the antagonist with respect to the receptor and desolvation effects at the receptor. The most active compound in the series is the 2-amino-3-nitropyrrole derivative 5, which combines a near-optimal dipole orientation with high lipophilicity.

  DOI：

  10.1021/jm00151a007

文献信息

• 2-(Substituted amino)-3-nitro-2,3-unsaturated nitrogen heterocycles
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04238493A1

  公开（公告）日：1980-12-09

  2,3-Unsaturated nitrogen-containing heterocyclic compounds with a 3-nitro group and a 2-heterocyclyl alkylamino group. The alkyl group of 2-position substituents is preferably interrupted by sulfur or oxygen. The compounds of the invention are preferably dihydropyrroles or tetrahydropyridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.

  含有3-硝基和2-杂环烷基氨基基团的2,3-不饱和氮杂环化合物。2-位置取代基的烷基基团最好由硫或氧中断。本发明的化合物最好是二氢吡咯或四氢吡啶或嘧啶。本发明的化合物是组胺H.sub.2-受体拮抗剂。
• The dielectric properties of seven polar amidine-containing compounds of biological interest
  作者：Rodney C. Young、C.Robin Ganellin、Michael J. Graham、Michael L. Roantree、Edward H. Grant

  DOI：10.1016/s0040-4039(00)94768-3

  日期：1985.1

  The static permittivities of seven polar molecules of biological interest have been determined in water and ethane diol, and estimates have been made of their effective dipole moments.

  在水和乙二醇中已经确定了七个具有生物学意义的极性分子的静电电容，并对其有效偶极矩进行了估算。
• 2-thiazolyl, oxazolyl, triazolyl and thiadiazolyl
  申请人：SmithKline & French Laboratories Limited

  公开号：US04656176A1

  公开（公告）日：1987-04-07

  2,3-Unsaturated nitrogen-containing heterocyclic compounds with a 3-nitro group and a 2-heterocyclyl alkylamino group. The alkyl group of 2-position substituents is preferably interrupted by sulfur or oxygen. The compounds of the invention are preferably dihydropyrroles or tetrahydropyrridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.

  具有3-硝基和2-杂环烷基氨基基团的2,3-不饱和含氮杂环化合物。2-位置取代基的烷基团最好由硫或氧中断。本发明的化合物最好是二氢吡咯或四氢吡啶或嘧啶。本发明的化合物是组胺H.sub.2-受体拮抗剂。
• Nitro-substituted dihydropyrroles and tetrahydropyridines, compositions,
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04405624A1

  公开（公告）日：1983-09-20

  2,3-Unsaturated nitrogen-containing heterocyclic compounds with a 3-nitro group and a 2-heterocyclyl alkylamino group. The alkyl group of 2-position substituents is preferably interrupted by sulfur or oxygen. The compounds of the invention are preferably dihydropyrroles or tetrahydropyrridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.

  具有3-硝基和2-杂环基烷基氨基基团的2,3-不饱和含氮杂环化合物。2-位置取代基的烷基基团最好被硫或氧中断。本发明的化合物最好是二氢吡咯或四氢吡啶或嘧啶。本发明的化合物是组胺H.sub.2-受体拮抗剂。
• 2-Thiazolyl, isothiazolyl, oxazolyl and isoxazolyl
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04525477A1

  公开（公告）日：1985-06-25

  2,3-Unsaturated nitrogen-containing heterocyclic compounds with a 3-nitro group and a 2-heterocyclyl alkylamino group. The alkyl group of 2-position substituents is preferably interrupted by sulfur or oxygen. The compounds of the invention are preferably dihydropyrroles or tetrahydropyrridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.

  具有3-硝基和2-杂环基烷基氨基的2,3-不饱和含氮杂环化合物。2-位置取代基的烷基基团最好被硫或氧所间断。本发明化合物最好是二氢吡咯或四氢吡啶或嘧啶。本发明化合物是组胺H.sub.2-受体拮抗剂。