Wasson, B. K. published the artcileβ-Adrenergic blocking agents. 3-(3-Substituted-amino-2-hydroxypropoxy)-4-substituted-1,2,5-thiadiazoles, Category: alcohols-buliding-blocks, the publication is Journal of Medicinal Chemistry (1972), 15(6), 651-5, database is CAplus and MEDLINE.
A number of 3-(3-substitute-amino-2-hydroxypropoxy)-4-substituted-1,2,5-thiadiazoles were prepared by 3 general procedures: (a) by condensation of the appropriate 3-hydroxy-4-substituted-1,2,5-thiadiazole with epichlorohydrin, then formation of the epoxide, and condensation with an amine, (b) by treatment of 4-chloro-3-(3-substituted-amino-2-hydroxypropoxy)-1,2,5-thiadiazole with a heterocyclic compound containing a secondary N, or (c) by formation of a bromohydrin of a 3-substituted-4-allyloxy-1,2,5-thiadiazole, followed by treatment with an amine. A number of I containing 4-Cl, 4-Et, or 4-EtO such as (+)-3-(3-tert-butylamino-2-hydroxypropoxy)-4-chloro-1,2,5-thiadiazole-HCl [(+)-I, R = Cl, R1 = H, R2 = tert-Bu] [26791-14-0], 3-(3-isopropylamino-2-hydroxypropoxy)-4-ethyl-1,2,5-thiadiazole-HCl (I, R = Et, R1 = H, R2 = iso-Pr) [26670-38-2] and 3-(3-isopropylamino-2-hydroxypropoxy)-4-ethoxy-1,2,5-thiadiazole-HCl (I, R = EtO, R1 = H, R2 = iso-Pr) [26852-60-8] were potent β-adrenergic blocking agents but short acting (ED50 0.023, 0.04 and 0.035 mg/kg i.v., resp., dose required to inhibit by 50% the cardioaccelerator response to 0.12 mg/kg i.v. isoproterenol in the ganglion-blocked anesthetized rat). A number of 1,2,5-thiadiazoles possessing a bulky group in the 4-position were long acting, the outstanding member being (+-)-3-(3-tert-butylamino-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazole-HCl [(+-)-II -HCl] [26670-02-0] with an ED50 of 0.013. Resolution of (+-)-II showed the bulk of activity resided in the (+)-form, (+)-3-(3-tert-butylamino-2-hydroxypropoxy)-4-morpholino-1,2,5-thiadiazole hydrogen maleate [(+)-II H maleate] [26839-77-0] the ED50 being 0.0066. The optimal activity in the thiadiazoles was achieved by the presence of an iso-Pr or tert-Bu group in the aminoisopropanoloxy side chain and inclusion of a bulky substituent in the 4 position.
Journal of Medicinal Chemistry published new progress about 30165-97-0. 30165-97-0 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Thiadiazole,Alcohol, name is 4-Morpholino-1,2,5-thiadiazol-3-ol, and the molecular formula is C42H63O3P, Category: alcohols-buliding-blocks.
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