2-amino-4-methyl-5-(3-(naphthalen-1-yl)propyl)-thiophene-3-carbonitrile | 602330-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-4-methyl-5-(3-(naphthalen-1-yl)propyl)-thiophene-3-carbonitrile
• 英文别名: 2-Amino-4-methyl-5-(3-naphthalen-1-ylpropyl)thiophene-3-carbonitrile
• CAS: 602330-65-4
• 化学式: C₁₉H₁₈N₂S
• 分子量: 306.431
• InChiKey: ZXZNBUMYCYPNHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲脒盐酸盐 、 2-amino-4-methyl-5-(3-(naphthalen-1-yl)propyl)-thiophene-3-carbonitrile 反应 0.5h， 以84%的产率得到5-Methyl-6-(3-naphthalen-1-yl-propyl)-thieno[2,3-d]pyrimidine-2,4-diamine
  参考文献：
  名称：

  Synthesis and DHFR inhibitory activity of a series of 6-substituted-2,4-diaminothieno[2,3-d]pyrimidines

  摘要：

  A series of 6-aralkyl substituted 2,4-diaminothieno[2,3-d]pyrimidines in which the 6-aryl group is separated from the thieno[2,3-d]pyrimidine ring by two to five methylene groups were synthesized and studied as inhibitors of dihydrofolate reductase from Pneumocystis carinii, Toxoplasma gondii, Mycobacterium avium, and rat liver. Compounds in which the thieno[2,3-d]pyrimidine ring is separated from the 6-aryl substituent by three methylene groups were the most potent inhibitors of the series (with IC50 values ranging from 0.24 and 11.0 muM) but those with two methylene groups between the aromatic rings were the most selective agents. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00101-6
• 作为产物：
  描述：

  3-(naphthalen-1-yl)propanal 在 palladium on activated charcoal ammonium acetate 、 氢气 、 sulfur 、 溶剂黄146 、 二异丙胺 作用下， 以 乙醇 、 氯仿 、 苯 为溶剂， 反应 10.75h， 生成 2-amino-4-methyl-5-(3-(naphthalen-1-yl)propyl)-thiophene-3-carbonitrile
  参考文献：
  名称：

  Synthesis and DHFR inhibitory activity of a series of 6-substituted-2,4-diaminothieno[2,3-d]pyrimidines

  摘要：

  A series of 6-aralkyl substituted 2,4-diaminothieno[2,3-d]pyrimidines in which the 6-aryl group is separated from the thieno[2,3-d]pyrimidine ring by two to five methylene groups were synthesized and studied as inhibitors of dihydrofolate reductase from Pneumocystis carinii, Toxoplasma gondii, Mycobacterium avium, and rat liver. Compounds in which the thieno[2,3-d]pyrimidine ring is separated from the 6-aryl substituent by three methylene groups were the most potent inhibitors of the series (with IC50 values ranging from 0.24 and 11.0 muM) but those with two methylene groups between the aromatic rings were the most selective agents. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00101-6

文献信息

• NOVEL ANTI-CANCER THIOPHENE COMPOUNDS
  申请人：Katholieke Universiteit Leuven

  公开号：EP2864312B1

  公开（公告）日：2021-09-22
• Synthesis and DHFR inhibitory activity of a series of 6-substituted-2,4-diaminothieno[2,3-d]pyrimidines
  作者：I Donkor

  DOI：10.1016/s0223-5234(03)00101-6

  日期：2003.6

  A series of 6-aralkyl substituted 2,4-diaminothieno[2,3-d]pyrimidines in which the 6-aryl group is separated from the thieno[2,3-d]pyrimidine ring by two to five methylene groups were synthesized and studied as inhibitors of dihydrofolate reductase from Pneumocystis carinii, Toxoplasma gondii, Mycobacterium avium, and rat liver. Compounds in which the thieno[2,3-d]pyrimidine ring is separated from the 6-aryl substituent by three methylene groups were the most potent inhibitors of the series (with IC50 values ranging from 0.24 and 11.0 muM) but those with two methylene groups between the aromatic rings were the most selective agents. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.