9-(benzyloxymethyl)-10-(cyclohexylimino)-7,9-diazaspiro[4.5]dec-2-ene-6,8-dione | 1466431-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 9-(benzyloxymethyl)-10-(cyclohexylimino)-7,9-diazaspiro[4.5]dec-2-ene-6,8-dione
• 英文别名: 10-Cyclohexylimino-9-(phenylmethoxymethyl)-7,9-diazaspiro[4.5]dec-2-ene-6,8-dione
• CAS: 1466431-58-2
• 化学式: C₂₂H₂₇N₃O₃
• 分子量: 381.475
• InChiKey: RPRIZFYLOUKKOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(benzyloxymethyl)-10-(cyclohexylimino)-7,9-diazaspiro[4.5]dec-2-ene-6,8-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、248.22 kPa 条件下， 反应 1.0h， 以73%的产率得到9-(benzyloxymethyl)-10-(cyclohexylimino)-7,9-diazaspiro[4.5]decane-6,8-dione
  参考文献：
  名称：

  Rapid Access to 10-(Cyclohexylimino)-7,9-diazaspiro[4.5]decane-6,8-dione Derivatives for HIV-1 Reverse Transcriptase Inhibition via Ruthenium-Catalyzed Ring-Closing Metathesis

  摘要：

  HIV-1 reverse transcriptase, a multifunctional enzyme critical in the viral replication process, is an important target for suppression of virus spread. To date, there has been considerable effort to develop drugs against this enzyme with high activity and specificity, notably TNK-651 and its derivatives. In order to further improve the efficacy and to explore the structure-activity relationship, we have introduced the diazaspiro[4.5]decane-6,8-dione scaffold, with both a pyrimidine and an alicyclic ring, and have synthesized several new compounds in this class. Appreciable overall yield was achieved with minimized purification of the intermediates. Several compounds were tested against HIV-1 reverse transcriptase in vitro using nevirapine as a reference. One compound showed potent inhibitory activity, with an IC50 value (ca. 1.65 M) comparable to that of nevirapine. Our synthetic method provides a rapid access to compounds in this class. Thus, many other similar compounds can be further studied in a timely and cost-effective manner.

  DOI：

  10.1055/s-0033-1339179
• 作为产物：
  描述：

  7-benzoyl-9-(benzyloxymethyl)-10-(cyclohexylimino)-7,9-diazaspiro[4.5]dec-2-ene-6,8-dione 在 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到9-(benzyloxymethyl)-10-(cyclohexylimino)-7,9-diazaspiro[4.5]dec-2-ene-6,8-dione
  参考文献：
  名称：

  Rapid Access to 10-(Cyclohexylimino)-7,9-diazaspiro[4.5]decane-6,8-dione Derivatives for HIV-1 Reverse Transcriptase Inhibition via Ruthenium-Catalyzed Ring-Closing Metathesis

  摘要：

  HIV-1 reverse transcriptase, a multifunctional enzyme critical in the viral replication process, is an important target for suppression of virus spread. To date, there has been considerable effort to develop drugs against this enzyme with high activity and specificity, notably TNK-651 and its derivatives. In order to further improve the efficacy and to explore the structure-activity relationship, we have introduced the diazaspiro[4.5]decane-6,8-dione scaffold, with both a pyrimidine and an alicyclic ring, and have synthesized several new compounds in this class. Appreciable overall yield was achieved with minimized purification of the intermediates. Several compounds were tested against HIV-1 reverse transcriptase in vitro using nevirapine as a reference. One compound showed potent inhibitory activity, with an IC50 value (ca. 1.65 M) comparable to that of nevirapine. Our synthetic method provides a rapid access to compounds in this class. Thus, many other similar compounds can be further studied in a timely and cost-effective manner.

  DOI：

  10.1055/s-0033-1339179