Multicomponent synthesis of 2,3-dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones: a novel heterocyclic scaffold with antibacterial activity

Abstract

A multicomponent reaction of 3-aminopyrazol-5-ones with substituted salicylic aldehydes and acetylacetic ester leading to the formation of novel 2,3-dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones was discovered. The elucidation of the reaction scope revealed that 5-aminopyrazoles, 3-amino-1,2,4-triazoles and 6-aminouracil could be used as the heterocyclic amine component. Selected heterocyclic products were found to possess notable antibacterial activities.

Design, synthesis, antifungal activity, and 3D-QSAR of coumarin derivatives

“…17) In contrast to the traditional methodology of using an organic solvent, water used as the solvent in this reaction was free of pollution and environmentally safe. Subsequently, as shown in Scheme 1, a wide range of target compounds, 3a-3e 18) and 4a-4e, 19) were all efficiently furnished by the Knoevenagel reaction too. The synthesized target compounds were purified by silica gel column chromatography (CC), and their structures were characterized by melting point (mp), FT-IR, 1 H-NMR, MS, or HRMS (for new compounds only).…”

An Efficient Synthesis of Coumarino[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives Catalyzed by Silica Sulfuric Acid under Microwave Irradiation

“…另外, 我们还考察了温度对反应 的影响, 发现在 100 ℃时反应的产率最高. 在上述优化 的条件下, 我们利用不同取代的 3-酰基香豆素和 5-氨基 吡唑反应合成了一系列香豆素并 [4,3-d] Entries 4,7,11,15,16 [4,3-d]pyrazolo [3,4-b] 4, 142.6, 142.0, 138.6, 132.6, 129.3, 128.9, 126.5, 123.6, 121.6, 117.2, 116.5, 110.4, 108.8, 28.1, 19.1;IR (KBr) ν: 3048, 2924, 1723, 1548, 1452, 1265, 1194, 1027 1, 160.1, 152.5, 151.9, 146.0, 142.0, 134.5, 132.4, 131.3, 129.5, 128.8, 128.6, 122.8, 116.5, 115.7, 110.3, 105.3, 34.2, 28.0 5, 152.5, 151.7, 147.2, 142.2, 138.9, 134.3, 132.4, 131.5, 129.7, 129.5, 129.2, 129.0, 128.6, 126.7, 122.7, 122.5, 122.0, 116.6, 115.6, 110.8, 106.8, 41.6, 22.0, 14. 166.3, 159.8, 152.5, 142.7, 132.5, 129.2, 123.5, 117.2, 116.9, 109.4, 100.0, 41.1, 33.7, 22.3, 19.0, 14.3;IR (KBr) ν: 2959, 2933, 2872, 1722, 1562, 1459, 1267, 1232, 1178, 1011 159.0, 151.9, 150.8, 141.2, 140.8, 132.2, 128.9, 128.4, 118.5, 118.0, 109.2, 106.6, 41.0, 33.7, 22.1, 19.1, 14.3;IR (KBr) ν: 2957, 2877, 1728, 1560, 1419, 1256, 1187, 1050 166.6, 158.8, 151.4, 151.3, 142.4, 140.9, 138.6, 135.1, 131.6, 129.0, 126.5, 121.5, 118.9, 118.3, 116.2, 110.1, 108.4, 41.0, 21.8, 19.1, 14.3;IR (KBr) ν: 2953, 2862, 1740…”

“…香豆素并 [4,3-d]吡唑并 [3,4-b]吡啶是一类具有很强荧光性质的多杂环化合物 [10] , 该 23% [10] . Magedov 等 [11] 利用哌啶作为催化剂和乙酸作溶 剂, 水杨醛、乙酰乙酸酯与 5-氨基吡唑的三组分反应合 成了该化合物, 收率只有 65%, 而且只报道了一个化合 物. 最近, 我们利用 CuCl 2 •2H 2 O 催化的 3-酰基香豆素与 5-氨基吡唑的反应改进了该化合物的合成 [12] , 虽然产率 有了明显的提高, 但是部分化合物的产率还只有中等 (63%), 而且有的反应时间还比较长(19.5 h), 所以该类 化合物的合成方法也有待于进一步改进.…”

Efficient One-Pot Synthesis of 1,4-Dihydropyridino[3,2-c]coumarins

“…香豆素衍生物是一类广泛存在于自然界中的重要 的杂环化合物, 具有明显的抗凝结、抗癌症及抗 HIV 等 生物活性 [4] . 其中吡啶并香豆素类化合物由于具有抑制 单胺氧化酶 [5] 、抗肿瘤 [6] 、止痛 [7] 、抗菌 [8] [9] (结构式 A), 二 氢喹啉并[3,2-c]香豆素 [10] (结构式 B), 具有抗肿瘤活性 的四氢喹啉并[3,2-c]香豆素 [11] (结构式 C)等, 成为香豆 素类化合物研究领域中的一个热点. 最近, 我们以稠杂环化合物为研究对象, 先后合成 了具有潜在生物活性的含吡啶 [12] 、吡喃 [13] 、呋喃 [14] 、香 豆素 [15] [17] 受到关注, 但在碘作用下的该类反应报道不 多 [18] .…”