Synthesis of Some Benzo-14-crown-4 Ethers Substituted to 7,8-Dihydroxy-3-phenylcoumarin Derivatives
摘要:
7,8-Dihydroxy-3-phenylcoumarin derivatives reacted with 1,2-bis-(3-tosyloxypropoxy)benzene in CH3CN/alkali carbonate to furnish 3-phenylchromenone-14-crown-4 ether derivatives, which were identified with elemental analysis, IR, H-1 NMR, C-13 NMR and MS spectroscopy.
The invention provides a compound having a 12-lipoxygenase inhibitory effect and a drug selectively inhibiting 12-lipoxygenase and relates to a novel coumarin derivative represented by general formula (1) and a drug comprising said compound as the active ingredient. In formula (1) R¹ represents hydrogen or lower alkyl; R² and R³ represent each hydrogen or hydroxyl provided that R² and R³ do not represent hydrogen atoms at the same time; and Ar represents (a) (b), (c) etc.; and R⁴ represents lower alkyl, lower alkoxy, halogen, trifluoromethyl or cyano. It further provides a compound which can be converted into another compound capable of selectively inhibiting 12-lipoxygenase activity through cleavage and breakage of its modifying moiety in vivo and a drug which selectively inhibits 12-lipoxygenase and relates to a novel coumarin derivative having an acyl group as the modifying moiety and a drug containing said compound as the active ingredient. The invention compound, which can potently inhibit 12-lipoxygenase at a high selectivity, is useful as a drug for preventing and treating circulatory diseases such as arteriosclerosis and vasoconstriction and preventing the metastasis of certain cancers. It has a low toxicity and little exhibits side effects.
Synthesis of Some Benzo-14-crown-4 Ethers Substituted to 7,8-Dihydroxy-3-phenylcoumarin Derivatives
作者:Ümit Salan、Mustafa Bulut
DOI:10.3987/com-05-10581
日期:——
7,8-Dihydroxy-3-phenylcoumarin derivatives reacted with 1,2-bis-(3-tosyloxypropoxy)benzene in CH3CN/alkali carbonate to furnish 3-phenylchromenone-14-crown-4 ether derivatives, which were identified with elemental analysis, IR, H-1 NMR, C-13 NMR and MS spectroscopy.
Investigation of HMG‐CoA reductase inhibitory and antioxidant effects of various hydroxycoumarin derivatives
low‐density lipoprotein cholesterol level is critical for treating these diseases, the inhibition of 3‐hydroxy‐3‐methyl‐glutaryl coenzyme A (HMG‐CoA) reductase, which is essentially responsible for cholesterolbiosynthesis, stands out as a key solution to lower plasma cholesterol levels. In this study, we synthesized several dihydroxycoumarins and investigated their antioxidant and in vitro HMG‐CoA reductase
心血管疾病是世界范围内死亡的主要原因之一,动脉粥样硬化的发展与高胆固醇血症密切相关。由于低密度脂蛋白胆固醇水平的降低对于治疗这些疾病至关重要,因此主要负责胆固醇生物合成的 3-羟基-3-甲基-戊二酰辅酶 A (HMG-CoA) 还原酶的抑制作用突出降低血浆胆固醇水平的关键解决方案。在这项研究中,我们合成了几种二羟基香豆素,并研究了它们的抗氧化和体外 HMG-CoA 还原酶抑制作用。此外,我们进行了计算机研究并检查了香豆素衍生物的量子化学性质。我们还进行了分子对接实验并分析了每种香豆素衍生物的结合强度。我们的结果表明,化合物 IV 在体外表现出最高的 HMG-CoA 还原酶抑制活性 (IC50 = 42.0 µM)。铜还原抗氧化能力和铁还原抗氧化能力测定表明香豆素衍生物表现出有效的抗氧化活性。此外,发现最低未占分子轨道能级与抗氧化活性之间存在密切关系。