5-氨基甲基-2-(4-氯苯基)噻吩 | 62403-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-氨基甲基-2-(4-氯苯基)噻吩
• 英文名称: 5-aminomethyl-2-(4-chlorophenyl)thiophene
• 英文别名: [5-(4-Chlorophenyl)thiophen-2-yl]methanamine
• CAS: 62403-51-4
• 化学式: C₁₁H₁₀ClNS
• 分子量: 223.726
• InChiKey: IIPNNQZFBHWKAI-UHFFFAOYSA-N

物化性质

• 沸点：
  341.1±32.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-(4-Chlorophenyl)thiophene-2-carboxamide	62404-24-4	C11H8ClNOS	237.71
  5-(4-氯苯基)噻吩-2-甲醛	5-(4-chlorophenyl)thiophene-2-carbaldehyde	38401-71-7	C11H7ClOS	222.695

反应信息

• 作为反应物：
  描述：

  5-氨基甲基-2-(4-氯苯基)噻吩 在 N,N-二异丙基乙胺 作用下， 以 乙醇 、 正丁醇 为溶剂， 生成 N⁴-((5-(4-chlorophenyl)thiophen-2-yl)methyl)-N²-isobutylpyrimidine-2,4-diamine
  参考文献：
  名称：

  Design, synthesis and evaluation of phenylthiazole and phenylthiophene pyrimidindiamine derivatives targeting the bacterial membrane

  摘要：

  As the continuous rise in the incidence of antibiotic resistance, it is urgent to develop novel chemical scaffolds with antibacterial activities to control the spread of resistance to conventional antibiotics. In this study, a series of phenylthiazole and phenylthiophene pyrimidindiamine derivatives were designed and synthesized by modifying the hit compound (N-2-isobutyl-N-4-((4-methyl-2-phenylthiazol-5-yl) methyl) pyrimidine-2,4-diamine) and their antibacterial activities were evaluated both in vitro and in vivo. Among the tested compounds, compound 14g (N4-((5-(3-bromophenyl)thiophen-2-yl)-methyl)N-2-isobutylpyrimidine-2,4-diamine) displayed the best antibacterial activities, which was not only capable of inhibiting E. coil and S. aureus growth at concentrations as low as 2 and 3 mu g/mL in vitro, but also efficacious in a mice model of bacteremia in vivo. Unlike conventional antibiotics, compound 14g was elucidated to mainly destroy the bacterial cell membrane, with the dissipation of membrane potential and leakage of contents, ultimately leading to cell death. The destruction of cell structure is challenging to induce bacterial resistance, which suggested that compound 14g may be a kind of promising alternatives to antibiotics against bacteria. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112141
• 作为产物：
  描述：

  5-(4-氯苯基)噻吩-2-甲醛 在 吡啶 、 盐酸羟胺 、 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 5-氨基甲基-2-(4-氯苯基)噻吩
  参考文献：
  名称：

  Design, synthesis and evaluation of phenylthiazole and phenylthiophene pyrimidindiamine derivatives targeting the bacterial membrane

  摘要：

  As the continuous rise in the incidence of antibiotic resistance, it is urgent to develop novel chemical scaffolds with antibacterial activities to control the spread of resistance to conventional antibiotics. In this study, a series of phenylthiazole and phenylthiophene pyrimidindiamine derivatives were designed and synthesized by modifying the hit compound (N-2-isobutyl-N-4-((4-methyl-2-phenylthiazol-5-yl) methyl) pyrimidine-2,4-diamine) and their antibacterial activities were evaluated both in vitro and in vivo. Among the tested compounds, compound 14g (N4-((5-(3-bromophenyl)thiophen-2-yl)-methyl)N-2-isobutylpyrimidine-2,4-diamine) displayed the best antibacterial activities, which was not only capable of inhibiting E. coil and S. aureus growth at concentrations as low as 2 and 3 mu g/mL in vitro, but also efficacious in a mice model of bacteremia in vivo. Unlike conventional antibiotics, compound 14g was elucidated to mainly destroy the bacterial cell membrane, with the dissipation of membrane potential and leakage of contents, ultimately leading to cell death. The destruction of cell structure is challenging to induce bacterial resistance, which suggested that compound 14g may be a kind of promising alternatives to antibiotics against bacteria. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112141

文献信息

• [EN] NOVEL PHENYL IMIDAZOLES AND PHENYL TRIAZOLES AS GAMMA-SECRETASE MODULATORS<br/>[FR] NOUVEAUX PHÉNYL IMIDAZOLES ET PHÉNYL TRIAZOLES EN TANT QUE MODULATEURS DE LA GAMMA SÉCRÉTASE
  申请人：PFIZER

  公开号：WO2010100606A1

  公开（公告）日：2010-09-10

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  所述化合物及其药用可接受盐已被披露，其中所述化合物具有规范中定义的Formula (I)的结构。相应的药物组合物、治疗方法、合成方法和中间体也已被披露。
• [EN] PYRIMIDINONE COMPOUNDS<br/>[FR] COMPOSES PYRIMIDINONES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2000066567A1

  公开（公告）日：2000-11-09

  Pyrimidinone compounds of formula (I) are inhibitors of the enzyme Lp-PLA2 and of use in therapy, in particular for treating atherosclerosis.

  公式(I)的嘧啶酮化合物是Lp-PLA2酶的抑制剂，并可用于治疗，特别是用于治疗动脉粥样硬化。
• Novel Phenyl Imidazoles and Phenyl Triazoles As Gamma-Secretase Modulators
  申请人：Allen Martin Patrick

  公开号：US20120053165A1

  公开（公告）日：2012-03-01

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  本发明公开了具有式（I）所定义的结构的化合物及其药学上可接受的盐，同时公开了相应的制药组合物、治疗方法、合成方法和中间体。
• GLYCOSYLATED GLYCOPEPTIDE ANTIBIOTIC DERIVATIVE
  申请人：Shionogi & Co., Ltd.

  公开号：EP2233495A1

  公开（公告）日：2010-09-29

  The present invention provides novel glycopeptides antibiotic derivatives. These glycopeptide antibiotic derivatives are characterized in that a sugar residue (I) represented by the formula: (wherein n is an integer of 1 to 5; Sugs are each independently a monosaccharide, (Sug)n is a divalent sugar residue formed by binding of same or different 1 to 5 monosaccharides; RA1 is optionally substituted lower alkyl, optionally substituted lower alkenyl, or optionally substituted cycloalkyl; and RE is OH or NHAc (Ac is acetyl)) is bound to an aromatic ring of the fourth amino acid residue in the glycopeptide skeleton. These derivatives have antibacterial activity against vancomycin-resistant bacteria.

  本发明提供了新型糖肽抗生素衍生物。 这些糖肽抗生素衍生物的特征在于由式（I）代表的糖残基： (其中n是1至5的整数；Sugs各自独立地是单糖，(Sug)n是由相同或不同的1至5单糖结合形成的二价糖残基；RA1是任选取代的低级烷基、任选取代的低级烯基或任选取代的环烷基；RE是OH或NHAc(Ac是乙酰基)) 与糖肽骨架中第四个氨基酸残基的芳香环结合。 这些衍生物对耐万古霉素细菌具有抗菌活性。
• BEATON C. M.; CHAPMAN N. B.; CLARKE K.; WILLIS J. M., J. CHEM. SOC. PERKIN TRANS., PART 1 <JCPK-BH>, 1976, NO 22, 2355-2363
  作者：BEATON C. M.、 CHAPMAN N. B.、 CLARKE K.、 WILLIS J. M.

  DOI：——

  日期：——