2-(7-bromo-3,5-dioxaheptylthio)-6-(3,5-dimethylbenzyl)-5-ethyl-pyrimidin-4(3H)-one | 261899-98-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(7-bromo-3,5-dioxaheptylthio)-6-(3,5-dimethylbenzyl)-5-ethyl-pyrimidin-4(3H)-one
• 英文别名: 2-[2-(2-bromoethoxymethoxy)ethylsulfanyl]-4-[(3,5-dimethylphenyl)methyl]-5-ethyl-1H-pyrimidin-6-one
• CAS: 261899-98-3
• 化学式: C₂₀H₂₇BrN₂O₃S
• 分子量: 455.416
• InChiKey: CTWLGMHIFXIQFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(7-bromo-3,5-dioxaheptylthio)-6-(3,5-dimethylbenzyl)-5-ethyl-pyrimidin-4(3H)-one 在 牛血清白蛋白 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以50%的产率得到4-(3,5-Dimethyl-benzyl)-3-ethyl-7,8-dihydro-6-oxa-9-thia-1,4a-diaza-benzocyclohepten-2-one
  参考文献：
  名称：

  Synthesis of 5-Alkyl-6-arylmethyl-2-(7-bromo-3,5-dioxaheptylthio)-pyrimidin-4(1H)-ones and 7-Oxopyrimidino-1,5,3-oxathiazepines as NewS-DABO Analogues with Anti-HIV Activity

  摘要：

  New S-DABOs with a long alkylating S-alkyl substituent showing antiretroviral activity against HIV-1 in the micromolar range were prepared from 5,6-disubstituted 4-oxo-2-thiopyrimidines and 1,7-dibromo-3,5-dioxaheptane. The analogues with an ethyl group in position 5 also showed activity in the micromolar range against a Tyr/8/Cys mutant strain of HIV-1. The S-DABO analogues showing activity against the HIV-1 RT mutant strain were transformed to the N-3 and N-1 ring closed 7-oxo-pyrimidino-1,3,5-oxathiazepines which surprisingly all showed activity against HIV-1 in the micromolar range, as well as against a Tyr/8/Cys mutant strain of HIV-1. Some analogues of S-DABO with a thien-7-ylmethyl residue in position 6 were synthesized and tested against HIV-1 wild type, hut they showed less or comparable activities to those of the corresponding 6-benzyl analogues.

  DOI：

  10.1007/s007060050310
• 作为产物：
  描述：

  1-Bromo-2-[(2-bromoethoxy)methoxy]ethane 、 6-(3,5-dimethylbenzyl)-5-ethyl-2,3-dihydro-2-thioxopyrimidin-4(1H)-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以75%的产率得到2-(7-bromo-3,5-dioxaheptylthio)-6-(3,5-dimethylbenzyl)-5-ethyl-pyrimidin-4(3H)-one
  参考文献：
  名称：

  Synthesis of 5-Alkyl-6-arylmethyl-2-(7-bromo-3,5-dioxaheptylthio)-pyrimidin-4(1H)-ones and 7-Oxopyrimidino-1,5,3-oxathiazepines as NewS-DABO Analogues with Anti-HIV Activity

  摘要：

  New S-DABOs with a long alkylating S-alkyl substituent showing antiretroviral activity against HIV-1 in the micromolar range were prepared from 5,6-disubstituted 4-oxo-2-thiopyrimidines and 1,7-dibromo-3,5-dioxaheptane. The analogues with an ethyl group in position 5 also showed activity in the micromolar range against a Tyr/8/Cys mutant strain of HIV-1. The S-DABO analogues showing activity against the HIV-1 RT mutant strain were transformed to the N-3 and N-1 ring closed 7-oxo-pyrimidino-1,3,5-oxathiazepines which surprisingly all showed activity against HIV-1 in the micromolar range, as well as against a Tyr/8/Cys mutant strain of HIV-1. Some analogues of S-DABO with a thien-7-ylmethyl residue in position 6 were synthesized and tested against HIV-1 wild type, hut they showed less or comparable activities to those of the corresponding 6-benzyl analogues.

  DOI：

  10.1007/s007060050310

文献信息

• Synthesis of 5-Alkyl-6-arylmethyl-2-(7-bromo-3,5-dioxaheptylthio)-pyrimidin-4(1H)-ones and 7-Oxopyrimidino-1,5,3-oxathiazepines as NewS-DABO Analogues with Anti-HIV Activity
  作者：Ole S. Pedersen、Lene Petersen、Malene Brandt、Claus Nielsen、Erik B. Pedersen

  DOI：10.1007/s007060050310

  日期：1999.12

  New S-DABOs with a long alkylating S-alkyl substituent showing antiretroviral activity against HIV-1 in the micromolar range were prepared from 5,6-disubstituted 4-oxo-2-thiopyrimidines and 1,7-dibromo-3,5-dioxaheptane. The analogues with an ethyl group in position 5 also showed activity in the micromolar range against a Tyr/8/Cys mutant strain of HIV-1. The S-DABO analogues showing activity against the HIV-1 RT mutant strain were transformed to the N-3 and N-1 ring closed 7-oxo-pyrimidino-1,3,5-oxathiazepines which surprisingly all showed activity against HIV-1 in the micromolar range, as well as against a Tyr/8/Cys mutant strain of HIV-1. Some analogues of S-DABO with a thien-7-ylmethyl residue in position 6 were synthesized and tested against HIV-1 wild type, hut they showed less or comparable activities to those of the corresponding 6-benzyl analogues.