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Calcium Dialkylamine Diazeniumdiolates: Synthesis, Stability, and Nitric Oxide Generation
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-20 , DOI: 10.1021/acs.joc.0c00020 Nabeelah I. Kauser 1 , Mark Weisel 2 , Yong-Li Zhong 2 , Michael Man-Chu Lo 1 , Amjad Ali 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-20 , DOI: 10.1021/acs.joc.0c00020 Nabeelah I. Kauser 1 , Mark Weisel 2 , Yong-Li Zhong 2 , Michael Man-Chu Lo 1 , Amjad Ali 1
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The therapeutic application of nitric oxide, an endogenous cellular signaling molecule, has been limited due to the difficulty of developing stable pro-drugs with slow kinetics of NO release. Diazeniumdiolates are valuable NO donors; however, synthetic challenges have hampered their use. O2-alkylation or arylation of diazeniumdiolates form stable pro-drugs which have found application in hypertension, cancer, and as antimicrobial agents. The synthesis of sodium diazeniumdiolates has proven to be challenging due to hazardous reaction conditions (high N2O concentrations, and flammable solvents), which can lead to detonation and suffered from limited scope. We have previously disclosed that synthesis of calcium diazeniumdiolate salts are a safer and more scalable alternative. Herein, we report the expanded scope of calcium diazeniumdiolates from benzylic amines, amides, and sterically bulky amines hitherto inaccessible and a comparison of their reactivity in comparison to sodium diazeniumdiolate.
中文翻译：
二烷基胺重氮二钙钙盐：合成，稳定性和一氧化氮的产生
一氧化氮（一种内源性细胞信号分子）的治疗应用受到限制，因为难以开发出具有缓慢NO释放动力学的稳定前药。二醇二氮烯鎓是有价值的NO供体；但是，合成挑战阻碍了它们的使用。二醇二氮烯鎓盐的O 2烷基化或芳基化形成稳定的前药，已发现它们可用于高血压，癌症和用作抗菌剂。由于危险的反应条件（高N 2O浓度和易燃溶剂），可能导致爆炸并受到范围限制。先前我们已经公开了二氮烯二钙钙盐的合成是更安全且可扩展的替代方案。在此，我们报道了迄今为止无法获得的苄基胺，酰胺和空间笨重的胺类二氮烯钙钙的扩大范围，并与二氮烯二醇钠进行了比较。
更新日期：2020-03-21
中文翻译：
二烷基胺重氮二钙钙盐：合成，稳定性和一氧化氮的产生
一氧化氮（一种内源性细胞信号分子）的治疗应用受到限制，因为难以开发出具有缓慢NO释放动力学的稳定前药。二醇二氮烯鎓是有价值的NO供体；但是，合成挑战阻碍了它们的使用。二醇二氮烯鎓盐的O 2烷基化或芳基化形成稳定的前药，已发现它们可用于高血压，癌症和用作抗菌剂。由于危险的反应条件（高N 2O浓度和易燃溶剂），可能导致爆炸并受到范围限制。先前我们已经公开了二氮烯二钙钙盐的合成是更安全且可扩展的替代方案。在此，我们报道了迄今为止无法获得的苄基胺，酰胺和空间笨重的胺类二氮烯钙钙的扩大范围，并与二氮烯二醇钠进行了比较。
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