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Azetidines
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Fragment-baseajord drug design has become a novel paradigm for drug discovery in the last decade. The lack of molecular rigidity intrinsic to a majority of small organic molecules appears to be a serious obstacle for this promising approach. Conformationally restricted rigid molecules show higher reproducibility of results when used in projects utilizing in silico screening methods. Due to a predefined spatial orientation of the molecular fragments mounted on a conformationally rigid scaffold, a decrease in entropy of molecular binding with its biological target might be expected, thus leading to higher affinity of the potential drug candidate.

One of the most popular approaches to limit molecular conformational flexibility relies on introduction of rings or ring systems. Small monocyclic scaffolds are preferable to other conformationally restricted scaffolds since their contribution to total molecular weight and lipophilicity of the molecule is less. Azetidine is the smallest nitrogen-containing saturated heterocycle possessing reasonable chemical stability. Azetidine-containing building blocks have been widely used for drug design for some time; one of the most successful examples includes calcium channel blocker Azelnidipine used as antihypertensive.

Azelnidipine

Reactive intermediates allowing introduction of small heterocycles like Azetidine are not widespread on the fine chemicals market. At the same time, ability to acquire such compounds for synthesis of a compound library can significantly speed up drug discovery project. Meeting this demand Enamine offers a set of azetidine-containing building blocks from stock. Example structures are shown in the table below. Please download database of azetidine-containing building blocks available from stock.

EN300-24071 EN300-27129 EN300-27423 EN300-30764
EN300-35928 EN300-35929 EN300-35930 EN300-37080
EN300-37081 EN300-37082 EN300-44244 EN300-39966
EN400-15244 EN400-15840 EN400-15841 EN400-15843

Additionally a set of azetidine-containing building blocks of general formula A – E is proposed for synthesis. Also over 200 compounds are offered for synthesis with fixed prices through joint Enamine-UORSY Library.

ABCD

E



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