3464-66-2Relevant articles and documents
Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b] indole-1-carboxylate: Concise synthesis of alangiobussinine
Baiget, Jessica,Llona-Minguez, Sabin,MacKay, Simon P.,Sutcliffe, Oliver B.,Lang, Stuart,Suckling, Colin J.
, p. 1407 - 1411 (2011)
The carboline ring system is an important pharmacophore found in a number of biologically important targets. Development of synthetic routes for the preparation of these compounds is important in order to prepare a range of analogues containing the carboline heterocyclic moiety. A manganese dioxide mediated one-pot method starting with an activated alcohol and consisting of alcohol oxidation, Pictet-Spengler cyclisation, and oxidative aromatisation, offers a convenient process that allows access to β-carbolines. This one-pot process for the preparation of methyl 9H-pyrido[3,4-b]indole-1- carboxylate has subsequently been used as the key step in the synthesis of alangiobussinine and a closely related analogue.
Facile synthesis of C1-substituted β-carbolines as CDK4 inhibitors for the treatment of cancer
Ding, Huaiwei,Huang, Yaoguan,Jia, Hui,Li, Deping,Liu, Mingyue,Liu, Wenwu,Lu, Hongyuan,Tian, Caizhi,Xu, Zihua,Zhao, Qingchun
, (2022/02/19)
Cyclin-dependent kinase 4 (CDK4), which is involved in dynamic regulation of cell cycle, has gained particularly attention for its role in controlling tumor growth. Increasing evidence showed that β-carboline derivatives have the potential to inhibit CDK4. Herein, on the basis of previous work, we designed and synthesized a series of novel β-carbolines and evaluated their antitumor activity. Among them, compounds ZDLD13 and ZDLD20, with the most potent anti-proliferative activity and CDK4 enzymatic inhibition activity, were selected for further pharmacological research in vitro and in vivo. The results in vitro showed that ZDLD13 and ZDLD20 exhibited potent anti-HCT116 activity including inhibition of colony formation, inhibition of invasion and migration, inducing of apoptosis, and arresting of G1 phase in cell cycle. In vivo, ZDLD13 showed significant tumor growth inhibition in HCT116 tumor xenograft model without causing significant weight loss and toxicity consistent with the acute toxicity test. In addition, silico study showed ZDLD13 and ZDLD20 not only have good biological actions, but also acceptable predicted ADME and physicochemical properties. Taken together, compounds ZDLD13 and ZDLD20 could be selected for further modification and preclinical evaluation.
Pityriacitrin alkaloid derivative containing acylthiourea structure as well as preparation method and application of pityriacitrin alkaloid derivative
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Paragraph 0032; 0034; 0041, (2021/08/21)
The invention discloses a pityriacitrin alkaloid derivative containing an acylthiourea structure as well as a preparation method and application of the pityriacitrin alkaloid derivative, and relates to a biocide of the pityriacitrin alkaloid derivative co
First total synthesis of the β-carboline alkaloids trigonostemine A, trigonostemine B and a new synthesis of pityriacitrin and hyrtiosulawesine
Szabó, Tímea,Hazai, Viktor,Volk, Balázs,Simig, Gyula,Milen, Mátyás
supporting information, p. 1471 - 1475 (2019/05/07)
The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtiosulawesine was accomplished. The key intermediates, variously substituted 1-formyl-β-carbolines, were prepared in five steps via a novel synthetic approach using readily available starting materials. These formyl derivatives were then further transformed, providing a general route for the synthesis of the four title alkaloids. The method reported herein represents the first total synthesis of the two trigonostemines and a new pathway to pityriacitrin and hyrtiosulawesine.
