1-苄基-2,5-二甲基-1H-吡咯-3-甲醛 | 56018-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-苄基-2,5-二甲基-1H-吡咯-3-甲醛
• 英文名称: 1-benzyl-2,5-dimethyl-3-formylpyrrole
• 英文别名: 1-benzyl-2,5-dimethyl-1H-pyrrole-3-carbaldehyde；1-Benzyl-2,5-dimethyl-pyrrol-3-carbaldehyd；1-benzyl-2,5-dimethyl-pyrrole-3-carbaldehyde；1-benzyl-2,5-dimethylpyrrole-3-carbaldehyde
• CAS: 56018-32-7
• 化学式: C₁₄H₁₅NO
• mdl: MFCD05998731
• 分子量: 213.279
• InChiKey: DRUVRRDEWCSBFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-甲基-2-甲基亚氨基-1,3-噻唑烷-4-酮 、 1-苄基-2,5-二甲基-1H-吡咯-3-甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-[(1-Benzyl-2,5-dimethylpyrrol-3-yl)methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype

  摘要：

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.049
• 作为产物：
  描述：

  1-苄基-2,5-二甲基吡咯 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 2.0h， 生成 1-苄基-2,5-二甲基-1H-吡咯-3-甲醛
  参考文献：
  名称：

  5,10-亚甲基四氢-5-脱氮磷酸及其类似物：合成和生物活性。

  摘要：

  据报道，5,10-亚甲基四氢叶酸（1）的稳定，刚性类似物5,10-亚甲基-5-脱氮基氢氢叶酸（2）的合成可能是胸苷酸合酶的抑制剂。通过从2-氨基-6-肼基-4-氧代嘧啶（10）和二乙基N- [4-（3-甲酰基-1-吡咯基）苯甲酰基]-的amino16的Fisher-吲哚型环化obtained得到目标化合物。 L-谷氨酸（15），然后催化还原产物17。类似地，对适当的前体11和12进行Fisher-吲哚型环化的修饰得到非经典类似物3-氨基-7,8,9-三甲基-2H -吡咯并[3'，4'：4,5]吡啶并[2,3-d]嘧啶-1-一（4）和3-氨基-8-苄基-7,9-二甲基-2H-吡咯并[3' ，4'：4,5]吡啶并[2,3-d]嘧啶-1-酮（5）。目标化合物2及其芳香族前体18 和非经典类似物4被评估为Manca人淋巴瘤细胞生长的抑制剂，也被评估为人二氢叶酸还原酶，人胸苷酸合酶，甘氨酰胺核糖核苷

  DOI：

  10.1021/jm00098a013

文献信息

• Novel indium-mediated deoxygenative α,α-diallylation of indole- and pyrrole-3-carboxaldehydes
  作者：Subodh Kumar、Vijay Kumar、Swapandeep Singh Chimni

  DOI：10.1016/s0040-4039(02)01973-1

  日期：2002.11

  1-Alkylindole-3-carboxaldehydes 1 and pyrrole-3-carboxaldehydes 2 on stirring with indium (2 equiv.) and allyl bromide (3 equiv.) in THF-H2O undergo deoxygenative diallylation at the carbonyl carbon to provide 3-[1,6-diene-4-yl]- indole 3 and pyrrole 4 derivatives. The formation of the normal 1,2-addition product in the case of 1d (R = COOEt) points towards the contribution of electronic factors due to the enamine double bond in the deoxygenation process. (C) 2002 Published by Elsevier Science Ltd.
• Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials
  作者：Dinakaran Murugesan、Alka Mital、Marcel Kaiser、David M. Shackleford、Julia Morizzi、Kasiram Katneni、Michael Campbell、Alan Hudson、Susan A. Charman、Clive Yeates、Ian H. Gilbert

  DOI：10.1021/jm400009c

  日期：2013.4.11

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.
• FRITZ H.; SCHENK S., J. LIEBIGS ANN. CHEM. <JLAC-BF>, 1975, NO 2, 255-265
  作者：FRITZ H.、 SCHENK S.

  DOI：——

  日期：——
• Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype
  作者：Mariangela Urbano、Miguel Guerrero、Subash Velaparthi、Melissa Crisp、Peter Chase、Peter Hodder、Marie-Therese Schaeffer、Steven Brown、Hugh Rosen、Edward Roberts

  DOI：10.1016/j.bmcl.2011.09.049

  日期：2011.11

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.
• 5,10-Methylenetetrahydro-5-deazafolic acid and analogs: synthesis and biological activities
  作者：Aleem Gangjee、Jasmin Patel、Roy L. Kisliuk、Yvette Gaumont

  DOI：10.1021/jm00098a013

  日期：1992.10

  precursors 11 and 12 afforded the nonclassical analogues 3-amino-7,8,9-trimethyl-2H-pyrrolo[3',4':4,5]pyrido[2,3-d]pyrimidin-1- one (4) and 3-amino-8-benzyl-7,9-dimethyl-2H-pyrrolo[3',4':4,5]pyrido [2,3-d]pyrimidin-1-one (5), respectively. The target compound 2, its aromatic precursor 18, and the nonclassical analogue 4 were evaluated as inhibitors of the growth of Manca human lymphoma cells and also as inhibitors

  据报道，5,10-亚甲基四氢叶酸（1）的稳定，刚性类似物5,10-亚甲基-5-脱氮基氢氢叶酸（2）的合成可能是胸苷酸合酶的抑制剂。通过从2-氨基-6-肼基-4-氧代嘧啶（10）和二乙基N- [4-（3-甲酰基-1-吡咯基）苯甲酰基]-的amino16的Fisher-吲哚型环化obtained得到目标化合物。 L-谷氨酸（15），然后催化还原产物17。类似地，对适当的前体11和12进行Fisher-吲哚型环化的修饰得到非经典类似物3-氨基-7,8,9-三甲基-2H -吡咯并[3'，4'：4,5]吡啶并[2,3-d]嘧啶-1-一（4）和3-氨基-8-苄基-7,9-二甲基-2H-吡咯并[3' ，4'：4,5]吡啶并[2,3-d]嘧啶-1-酮（5）。目标化合物2及其芳香族前体18 和非经典类似物4被评估为Manca人淋巴瘤细胞生长的抑制剂，也被评估为人二氢叶酸还原酶，人胸苷酸合酶，甘氨酰胺核糖核苷