1,2,3-Trihomodistamycin A | 85407-04-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,2,3-Trihomodistamycin A
• 英文别名: N-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-ethylpyrrol-3-yl]carbamoyl]-1-ethylpyrrol-3-yl]-1-ethyl-4-formamidopyrrole-2-carboxamide
• CAS: 85407-04-1
• 化学式: C₂₅H₃₃N₉O₄
• 分子量: 523.595
• InChiKey: GGMQCKNGZWEJLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  181
• 氢给体数：
  6
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[(4-Amino-1-ethyl-1H-pyrrole-2-carbonyl)-amino]-1-ethyl-1H-pyrrole-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、413.69 kPa 条件下， 反应 6.0h， 生成 1,2,3-Trihomodistamycin A
  参考文献：
  名称：

  Synthesis and antiviral activity of distamycin A analogs: substitutions on the different pyrrole nitrogens and in the amidine function

  摘要：

  Several new analogues of the antiviral antibiotic distamycin A were synthesized and assayed for their effects on influenza and herpes simplex virus. The new compounds 5b-j (R1-3 = H, CH3, and C2H5, R4,5 = H and CH3) were obtained via stepwise prepared formylated trimeric benzyl 4-aminopyrrole-2-carboxylates 3a-h, which after catalytic hydrogenolysis were coupled as N-succinimidyl esters directly with the proper beta-aminopropionamidine, unsubstituted or substituted with one or two methyl groups in the amidine function. Most of the new analogues did not exhibit significant effects on the viruses studied, but three compounds (5f-h) displayed activity on herpes virus as demonstrated in plaque formation and virus yield assays. Elevated cytotoxicity was simultaneously observed for 5g and 5h. For compound 5f, a partial separation of antiherpes activity and cytotoxicity was accomplished. The differences in antiherpes activity did not correspond to the differences in the inhibition of herpes virus DNA polymerase.

  DOI：

  10.1021/jm00361a018

文献信息

• Synthesis and antiviral activity of distamycin A analogs: substitutions on the different pyrrole nitrogens and in the amidine function
  作者：Leif Grehn、Ulf Ragnarsson、Bertil Eriksson、Bo Oeberg

  DOI：10.1021/jm00361a018

  日期：1983.7

  Several new analogues of the antiviral antibiotic distamycin A were synthesized and assayed for their effects on influenza and herpes simplex virus. The new compounds 5b-j (R1-3 = H, CH3, and C2H5, R4,5 = H and CH3) were obtained via stepwise prepared formylated trimeric benzyl 4-aminopyrrole-2-carboxylates 3a-h, which after catalytic hydrogenolysis were coupled as N-succinimidyl esters directly with the proper beta-aminopropionamidine, unsubstituted or substituted with one or two methyl groups in the amidine function. Most of the new analogues did not exhibit significant effects on the viruses studied, but three compounds (5f-h) displayed activity on herpes virus as demonstrated in plaque formation and virus yield assays. Elevated cytotoxicity was simultaneously observed for 5g and 5h. For compound 5f, a partial separation of antiherpes activity and cytotoxicity was accomplished. The differences in antiherpes activity did not correspond to the differences in the inhibition of herpes virus DNA polymerase.