Synthesis, Characterization and Antifungal Assessment of Optically Active Bis-organotin Compounds Derived from (S)-BINOL Diesters

Q2 Pharmacology, Toxicology and Pharmaceutics Open Medicinal Chemistry Journal Pub Date : 2019-05-31 DOI:10.2174/1874842201906010034
Andrea R Costantino, J. Neudörfl, Romina A. Ocampo, Laura A. Svetaz, S. Zacchino, L. Koll, Sandra D. Mandolesi
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引用次数: 3

Abstract

Organotin(IV) derivatives have appeared recently as potential biologically active metallopharmaceuticals exhibiting a variety of therapeutic activities. Hence, it is important to study the synthesis of new organotin compounds with low toxicity that may be of pharmacological interest. This study focuses on the synthesis of new bis-stannylated derivatives with C2 symmetry that could be tested as antifungal agents against two clinical important fungal species, Cryptococcus neoformans and Candida albicans. The radical addition of triorganotin hydrides (R3SnH) and diorganotin chlorohydrides (R2ClSnH) to bis-α,β-unsaturated diesters derived from (S)-BINOL led to the corresponding new bis-stannylated derivatives with C2 symmetry. Nine pure organotin compounds were synthesized with defined stereochemistry. Four of them were enantiomerically pure and four were diastereoisomeric mixtures. All new organotin compounds were fully characterized, those with phenyl ligands bonded to tin were the most active compounds against both the strains (Cryptococcus neoformans and Candida albicans), with activity parameters of IC50 close to those of the reference drug (amphotericin B). Nine pure organotin compounds with C2 symmetry were synthesized with defined stereochemistry and their antifungal properties were tested against two clinical important fungi with IC values close to those of the reference drug. The structure-containing preferably two or three phenyl groups joined to the tin atom were highly active against both the strains compared with those possessing tri-n-butyl groups.
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(S)-二醇二酯衍生的光学活性双有机锡化合物的合成、表征及抗真菌活性评价
有机锡(IV)衍生物近年来作为潜在的生物活性金属药物出现,表现出多种治疗活性。因此,研究合成可能具有药理价值的低毒性有机锡化合物是很重要的。本研究的重点是合成具有C2对称性的新型双锡化衍生物,该衍生物可作为抗两种临床重要真菌——新型隐球菌和白色念珠菌的抗真菌药物。三有机锡氢化物(R3SnH)和二有机锡氯化物(R2ClSnH)自由基加成到(S)-BINOL衍生的双-α,β-不饱和二酯上,得到相应的具有C2对称性的新双锡化衍生物。用确定的立体化学方法合成了9个纯有机锡化合物。其中4种为对映异构体纯,4种为非对映异构体混合物。所有新的有机锡化合物都得到了充分的表征,苯基配体与锡结合的化合物对两种菌株(新型隐球菌和白色念珠菌)都有最有效的抑制作用。合成了9个具有C2对称的纯有机锡化合物,并对两种临床重要真菌进行了抗真菌性能测试,其IC50值与对照药物(两性霉素B)的IC50值相近。与具有三正丁基基团的结构相比,结构上最好含有两个或三个苯基与锡原子连接的菌株对这两种菌株都具有高活性。
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来源期刊
Open Medicinal Chemistry Journal
Open Medicinal Chemistry Journal Pharmacology, Toxicology and Pharmaceutics-Pharmaceutical Science
CiteScore
4.40
自引率
0.00%
发文量
4
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