2-(5-ethylsulphonyl-2-methoxyphenyl)-1H-pyrrole | 110319-95-4

• 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-(5-ethylsulphonyl-2-methoxyphenyl)-1H-pyrrole
• 英文别名: 2-(2-methoxy-5-ethylsulfonylphenyl)pyrrole；2-(5-ethylsulfonyl-2-methoxyphenyl)-1H-pyrrole
• CAS: 110319-95-4
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: CDDVVZUJMPHDEG-UHFFFAOYSA-N

物化性质

• 熔点：
  130-133 °C
• 沸点：
  482.0±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰哌啶 、 2-(5-ethylsulphonyl-2-methoxyphenyl)-1H-pyrrole 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 生成 2-(5-ethylsulphonyl-2-methoxyphenyl)-5-[1-(1-piperidinyl)-ethyl)-1H-pyrrole
  参考文献：
  名称：

  Novel 2,5-disubstituted-1H-pyrroles with high affinity for the dopamine D3 receptor

  摘要：

  A series of 2,5-disubstituted-1H-pyrroles (4-18) has been prepared based on replacement of the amide of sultopride 1 by a pyrrole ring. Subsequent modification of the basic side chain gave compounds with high affinity for the dopamine D-3 receptor. In addition, 12 and 17 were shown to be D-3 antagonists with 30-fold selectivity for the D-3 receptor over the D-2 receptor. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00202-8
• 作为产物：
  描述：

  在 乙酸铵 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 17.5h， 生成 2-(5-ethylsulphonyl-2-methoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  Kruse, Chris G.; Bouw, Jan P.; Hes, Roelof van, Heterocycles, 1987, vol. 26, # 12, p. 3141 - 3151

  摘要：

  DOI：

文献信息

• 2-Phenylpyrroles as conformationally restricted benzamide analogs. A new class of potential antipsychotics. 2
  作者：Ineke Van Wijngaarden、Chris G. Kruse、Jan A. M. Van der Heyden、Martin T. M. Tulp

  DOI：10.1021/jm00118a011

  日期：1988.10

  A series of 2-phenylpyrrole Mannich bases was synthesized and screened in pharmacological models for antipsychotic activity and extrapyramidal effects. Structure modifications of 5-(4-fluorophenyl)-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]pyrrole (1), the prototype of a new class of sodium-independent atypical dopamine D-2 antagonists, resulted in 2-[[4-(7-benzofuranyl)-1-piperazinyl]methyl]-5

  合成了一系列2-苯基吡咯曼尼希碱，并在药理模型中筛选了抗精神病活性和锥体束外作用。5-（4-氟苯基）-2-[[4-（2-甲氧基苯基）-1-哌嗪基]甲基]吡咯的结构修饰（1），是新型的钠依赖性非典型多巴胺D-2拮抗剂的原型，产生2-[[[4-（7-苯并呋喃基）-1-哌嗪基]甲基] -5-（4-氟苯基）吡咯（15），它是比母体化合物更有效和选择性的D-2拮抗剂。阿朴吗啡诱导的攀爬行为具有出色的口服活性，并且有条件的回避反应测试以及没有僵住症，使得该化合物作为潜在的抗精神病药特别有前景，且诱发急性锥体外系副作用的可能性低。
• 5-(2-oxyphenyl)-pyrrole derivatives as dopamine D.sub.3 receptor
  申请人：SmithKline Beecham PLC

  公开号：US05523299A1

  公开（公告）日：1996-06-04

  Compounds of formula (I), ##STR1## wherein R.sup.1 represents C.sub.1-4 alkyl; and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently represent hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxyC.sub.1-4 alkyl, C.sub.1-4 alkylsulphonyl, trifluoromethylsulphonyl; optionally substituted arylsulphonyl, optionally substituted heteroarylsulphonyl, optionally substituted aralkylsulphonyl, optionally substituted heteroaralkylsulphonyl, nitro, cyano, amino, mono- or di-alkylamino, trifluoromethyl, trifluoromethoxy, hydroxyl, hydroxyalkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkanoyl, C.sub.1-4 alkoxycarbonyl, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl; or R.sup.1 and R.sup.2 together form a linking chain-(CH.sub.2).sub.m Op (wherein m is 2 to 4 and p is zero or 1) which chain may be optionally substituted by one or two C.sub.1-4 alkyl groups; and Y represents a group selected from (a) or (b) wherein R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.1-6 alkyl, optionally substituted arylC.sub.1-6 alkyl or optionally substituted heteroarylC.sub.1-6 alkyl; R.sup.8 represents C.sub.1-6 alkyl, C.sub.3-6 alkenyl or C.sub.3-6 cycloalkylC.sub.1-4 alkyl; and R.sup.9 represents C.sub.1-6 alkyl; C.sub.3-6 alkenyl; C.sub.3-6 cycloalkylC.sub.1-4 alkyl, optionally substituted arylC.sub.1-4 alkyl or optionally substituted heteroarylC.sub.1-4 alkyl; or NR.sup.8 R.sup.9 forms a heterocyclic ring (with the proviso that NR.sup.8 R.sup.9 is not piperazine); R.sup.10 represents C.sub.1-6 alkyl; C.sub.3-6 alkenyl; C.sub.3-6 cycloalkylC.sub.1-4 alkyl, optionally substituted arylC.sub.1-4 alkyl, or optionally substituted heteroarylC.sub.1-4 alkyl; and n is 1 to 3; and salts thereof, have affinity for dopamine D.sub.3 receptors and may be useful in the treatment of e.g., psychotic disorders.

  式(I)的化合物，其中R.sup.1代表C.sub.1-4烷基；而R.sup.2、R.sup.3、R.sup.4和R.sup.5分别独立地代表氢、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基、C.sub.1-4烷氧基C.sub.1-4烷基、C.sub.1-4烷基磺酰基、三氟甲基磺酰基；可选择地取代的芳基磺酰基、可选择地取代的杂环芳基磺酰基、可选择地取代的芳基烷基磺酰基、可选择地取代的杂环烷基磺酰基、硝基、氰基、氨基、单烷基或双烷基氨基、三氟甲基、三
• Palladium(0)-Catalysed Arylations using Pyrrole and Indole 2-Boronic Acids
  作者：Christopher N. Johnson、Geoffrey Stemp、Neel Anand、Susanna C. Stephen、Timothy Gallagher

  DOI：10.1055/s-1998-1834

  日期：1998.9

  A versatile synthesis of 2-arylpyrroles and 2-arylindoles is described based on the use of either N-(Boc) pyrrole-2-boronic acid or N-(Boc) indole-2-boronic acid as components for Suzuki coupling.

  以 N-(叔丁氧羰基)吡咯-2-硼酸或 N-(叔丁氧羰基)吲哚-2-硼酸作为铃木偶联的组分，介绍了 2-芳基吡咯和 2-芳基吲哚的多功能合成方法。
• Phenyl, Pyrrolidin-2-yl substituted pyrroles having antipsychotic
  申请人：Duphar International Research B.V.

  公开号：US04791132A1

  公开（公告）日：1988-12-13

  The invention relates to a group of new phenyl, pyrrolidin-2-yl substituted 5-ring heterocyclic compounds of the formula ##STR1## wherein A is an unsaturated heterocyclic 5-ring having at least one nitrogen or oxygen atom in the ring, with the proviso that the phenyl substituent is in a meta-position with respect to the 2-pyrrolidinyl substituent. The compounds have interesting pharmacological, notably antipsychotic properties.

  本发明涉及一组新的苯基、吡咯烷-2-基取代的5元杂环化合物，其分子式为：##STR1## 其中，A是一种不饱和的5元杂环，其环中至少有一个氮或氧原子，且苯基取代基与2-吡咯烷基取代基的相对位置为间位。这些化合物具有有趣的药理学特性，尤其是抗精神病作用。
• 2-phenylpyrrole derivatives as dopamine D.sub.3 receptor antagonists
  申请人：SmithKline Beecham plc

  公开号：US05637609A1

  公开（公告）日：1997-06-10

  A compound of formula (I): ##STR1## which have high affinity for dopamine D.sub.3 receptors and thus have potential as antipsychotic agents.

  化合物的公式（I）：##STR1## 其具有高亲和力与多巴胺D.sub.3受体，因此具有作为抗精神病药物的潜力。