34576-98-2Relevant academic research and scientific papers
Discovery of novel simplified isoxazole derivatives of sampangine as potent anti-cryptococcal agents
Li, Zhuang,Liu, Na,Tu, Jie,Ji, Changjin,Han, Guiyan,Wang, Yan,Sheng, Chunquan
, p. 832 - 840 (2019/02/03)
Cryptococcus neoformans is the leading cause of cryptococcal meningitis, which is associated with high mortality due to lack of effective treatment. Herein a series of tricyclic isoxazole derivatives with excellent anti-cryptococcal activities were identi
Tricycloisoxazole compound and preparation and application methods thereof
-
Paragraph 0127; 0129, (2019/03/31)
The invention discloses a tricycloisoxazole compound and a medically acceptable salt thereof. The structure of the tricycloisoxazole compound is shown as the formula I, wherein A is thienyl, furyl, phenyl and pyridyl; R1 is hydrogen, halogen, amido, substituted amido, nitro, acylamino, substituted acylamino, cyan, low alkyl and alkoxy; R2 is alkyl, alkoxy, alkoxy alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclyl; R3 is carbon or hydroxyl; X is carbon atom or oxygen atom, and when being carbon atom, is connected with the substituted group R3, which is carbonyl or carboxyl. The invention also provides preparation and application methods of the tricycloisoxazole compound, namely, the tricycloisoxazole compound can serve as an antifungal small-molecule inhibitor. In vitro antifungal activity experiment results show that most of the tricycloisoxazole compound shown as the formula I achieves good antifungal activity, especially significantly higher antifungal activity on Cryptococcus neoformans compared with a positive fungicide of fluconazole, thereby being applicable to preparing antifungal drugs.
Discovery of simplified sampangine derivatives as novel fungal biofilm inhibitors
Liu, Na,Zhong, Hua,Tu, Jie,Jiang, Zhigan,Jiang, Yanjuan,Jiang, Yan,Jiang, Yuanying,Li, Jian,Zhang, Wannian,Wang, Yan,Sheng, Chunquan
, p. 1510 - 1523 (2017/11/13)
Lack of novel antifungal agents and severe drug resistance have led to high incidence and associated mortality of invasive fungal infections. To tackle the challenges, novel antifungal agents with new chemotype, fungicidal activity and anti-resistant potency are highly desirable. On the basis of our previously identified simplified analogue of antifungal natural product sampangine, systemic structure-activity relationships were clarified and two novel derivatives showed promising features as novel antifungal lead compounds. Compounds 22b and 22c showed good fungicidal activity against both fluconazole-sensitive and fluconazole-resistant Candida albicans strains. Moreover, they were proven to be potent inhibitors of Candida albicans biofilm formation and yeast-to-hypha morphological transition by down-regulating biofilm-associated genes. In a rat vaginal Candida albicans infection model, compounds 22b and 22c showed excellent therapeutic effects with low toxicity. The results highlighted the potential of sampangine derivatives to overcome fluconazole-related and biofilm-related drug resistance.
Substituted thiophene and benzoquinone and isoxazole compound and its preparation method and application
-
Paragraph 0034; 0120; 0121, (2017/07/23)
The invention relates to the technical field of medicine, and provides substituted tricyclo-quinone compounds and pharmaceutically acceptable salts thereof. The structural general formula of the substituted aromatic tetracyclic compounds is disclosed in the specification. The invention also provides a preparation method of the compounds and application of the compounds in preparation of antifungal drugs.
Substituted aromatic four ring anti-fungal compound and its preparation method and application
-
Paragraph 0097; 0098, (2016/10/08)
The invention relates to the technical field of pharmaceuticals, and provides a substituted aryl tetracyclic antifungal compound and pharmaceutically acceptable salts. The substituted aryl tetracyclic antifungal compound is as shown in a structural formula of the description. The invention further provides a preparation method of the compound and an application of the compound in preparing antifungal medicaments.
Scaffold hopping of sampangine: Discovery of potent antifungal lead compound against Aspergillus fumigatus and Cryptococcus neoformans
Jiang, Zhigan,Liu, Na,Dong, Guoqiang,Jiang, Yan,Liu, Yang,He, Xiaomeng,Huang, Yahui,He, Shipeng,Chen, Wei,Li, Zhengang,Yao, Jianzhong,Miao, Zhenyuan,Zhang, Wannian,Sheng, Chunquan
, p. 4090 - 4094 (2014/09/17)
Discovery of novel antifungal agents against Aspergillus fumigatus and Cryptococcus neoformans remains a significant challenge in current antifungal therapy. Herein the antifungal natural product sampangine was used as the lead compound for novel antifungal drug discovery. A series of D-ring scaffold hopping derivatives were designed and synthesized to improve antifungal activity and water solubility. Among them, the thiophene derivative S2 showed broad-spectrum antifungal activity, particularly for Aspergillus fumigatus and Cryptococcus neoformans. Moreover, compound S2 also revealed better water solubility than sampangine, which represents a promising antifungal lead compound for further structural optimization.
An Efficient Route to Benzothiophene Quinones, Quinone Bisketals, and Quinone Monoketals via Anodic Oxidation of Methoxylated Benzothiophenes. Studies Directed at the Synthesis of Functionalized Benzothiophene-4,7-quinones
Chenard, Bertrand L.,McConnell, J. Russell,Swenton, John S.
, p. 4312 - 4317 (2007/10/02)
A convenient route to 4-and 7-methoxybenzothiophenes has been developed in the course of electrochemical studies of these molecules.The anodic oxidations of 4-methoxy-, 5-bromo-4-methoxy-, 5-methyl-4-methoxy-, and 6-bromo-7-methoxybenzothiophene, 17a-d, respectively, in methanolic potassium hydroxide at a platinum anode have been investigated.The products obtained from the oxidation of these compounds were temperature dependent.This temperature dependence was most extensively studied for 17a wherein oxidation at or below room temperature, followed by workup, gave primarily 4,7-dimethoxybenzothiophene.However, oxidation of 17a in methanol at ca. 65 deg C gave primarily the quinone bisketal.In a similar manner oxidation of 17b,c gave the respective bisketals of benzothiophene-4,7-quinones in good yields.Extended acidic hydrolyses of these quinone bisketals afforded the corresponding quinones in 78-95 percent yield.Milder conditions for the hydrolyses afforded monoketals of benzothiophene-4,7-quinones, the products from 17b,c being formed with high regioselectivity.Other chemistry of these quinone bis- and monoketals, initially directed at a synthesis of Caldariellaquinone, is presented and discussed.
