De novo design and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions.
De novo design and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions.
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二吡啶并嘌呤酮衍生物作为可见光光催化剂在高效鸟苷化反应中的从头设计和合成
DOI：
10.1039/d1sc05294b
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发表时间：
2021-12-15
期刊：
影响因子：
8.4
通讯作者：
Zhang G
中科院分区：
文献类型：
--
作者：
Wan Y;Wu H;Ma N;Zhao J;Zhang Z;Gao W;Zhang G
设计并合成了一系列6 H-联吡啶并[1，2-e：2′，1 ′-i]嘌呤-6-酮（DP）可见光光氧化还原催化剂。合成的DP 1 -5的λAbs（max）值在433-477 nm，激发态氧化还原电位分别在1.15-0.69 eV和−1.41-−1.77 eV（vs. SCE）。作为代表，DP 4能够使各种胺（包括1°、2°和3°-烷基伯胺、仲胺、芳基和杂芳基胺、氨基腈、氨基酸和肽以及丙炔胺和α-氨基酯）的生产性胍基化，从而在生物学上重要的胍和环胍中产生二氢胍。DP 4在鸟苷基化中的光催化效率超过了常用的Ir和Ru多吡啶配合物和一些有机PC。该方法的其他突出优点包括广泛的底物范围和官能团耐受性、克级合成和多功能的后期衍生化，其导致衍生物81对拉莫斯细胞表现出60倍更好的抗癌活性，其IC 50为0.086 μM，比临床药物伊曲替尼（5.1 μM）高。设计了一种新型的可见光催化剂，其在胺的胍基化反应中的光催化效果优于普通的金属核和有机光催化剂。
Described here is the de novo design and synthesis of a series of 6H-dipyrido[1,2-e:2′,1′-i]purin-6-ones (DPs) as a new class of visible-light photoredox catalysts (PCs). The synthesized DP1–5 showed their λAbs(max) values in 433–477 nm, excited state redox potentials in 1.15–0.69 eV and −1.41 to −1.77 eV (vs. SCE), respectively. As a representative, DP4 enables the productive guanylation of various amines, including 1°, 2°, and 3°-alkyl primary amines, secondary amines, aryl and heteroaryl amines, amino-nitrile, amino acids and peptides as well as propynylamines and α-amino esters giving diversities in biologically important guanidines and cyclic guanidines. The photocatalytic efficacy of DP4 in the guanylation overmatched commonly used Ir and Ru polypyridyl complexes, and some organic PCs. Other salient merits of this method include broad substrate scope and functional group tolerance, gram-scale synthesis, and versatile late-stage derivatizations that led to a derivative 81 exhibiting 60-fold better anticancer activity against Ramos cells with the IC50 of 0.086 μM than that of clinical drug ibrutinib (5.1 μM). A novel visible-light photocatalyst was designed and its photocatalytic efficacy in the guanylation of amines overmatched common metal-core and organic photocatalysts.
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影响因子：
18.3
作者：
Beatty, Joel W.;Stephenson, Corey R. J.
通讯作者：
Stephenson, Corey R. J.
影响因子：
7.3
作者：
Carpenter, Richard D.;Andrei, Mirela;Kurth, Mark J.
通讯作者：
Kurth, Mark J.
影响因子：
16.6
作者：
Buss, Bonnie L.;Lim, Chern-Hooi;Miyake, Garret M.
通讯作者：
Miyake, Garret M.
影响因子：
7.3
作者：
Bonfanti, Jean-Francois;Meyer, Christophe;Andries, Koen
通讯作者：
Andries, Koen
影响因子：
1.8
作者：
Bhagat, Saket B.;Telvekar, Vikas N.
通讯作者：
Telvekar, Vikas N.