Abstract
A novel class of aminopyrrolidinyl phosphonates was synthesized in 74% - 80% isolated yield by the addition of three-fold excess of primary amines to diethyl 4-chloro-1-butynylphosphonates. The reaction was carried out at room temperature and in the absence of solvent or catalyst to give solely compounds which showed predicted biological activity based on PASS program. Some of the synthesized derivatives of antibiotics exhibit properties for the treatment of stroke, the treatment of acute neurological disorders, and can also be acetyl esterase inhibitors.
Highlights
Natural antibiotics are produced by many microorganisms and are of great interest in medicine and pharmacology [1] [2] [3] [4]
A novel class of aminopyrrolidinyl phosphonates was synthesized in 74% 80% isolated yield by the addition of three-fold excess of primary amines to diethyl 4-chloro-1-butynylphosphonates
It is well known that some antibiotics, such as K-26, SF-2513, FR-33289, and SF-2312 contain a C-P bond that belongs to the category of phosphonates [5] [6] [7] [8]
Summary
Natural antibiotics are produced by many microorganisms and are of great interest in medicine and pharmacology [1] [2] [3] [4]. Few pyrrolidinylphosphonates and pyrrolidinylphosphonic acids (1-12, Figure 1) were synthesized for the purpose of testing their biological activity They were obtained either from readily available pyrrolidine ring or by multistep cyclization reactions. There is no one general direct method to produce them and a brief summary for their synthesis is described below: Initially, the antibiotic SF-2312 (1) and its analogue (3) were synthesized by a multistep reaction sequence in which ethyl diethoxyphosphorylacetate was converted to N-benzyloxy-2-(diethoxyphosphoryl)-pent-4-enamide followed by oxidative cleavage and hydrolysis [21]. The SF-2312 (1) antibiotic analogues (7-10) were obtained using 1-benzyloxy-3-bromopyrrolidin-2,5-dione through Michaelis-Arbusov reaction with trialkyl phosphites followed by alkylation Their biological activity was not determined [19] [20]. Three-component decarboxylative coupling of proline with aldehydes and dialkyl phosphite was used to afford the corresponding pyrrolidinylphosphonates (12) [33]
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