Vasicine hydrochloride

The passage of gaseous hydrogen chloride into a dry methanolic solution of 191 resulted in the formation of vasicine hydrochloride (184-HCl). Treatment of 191 with phosphoryl chloride in pyridine afforded the 3-chlo-ropyrrolo[2,l- )]quinazoline 336. ... 

The uterotonic activity of vasicine (184) was investigated in detail on the uteri of diflferent animal species and on human myometrium." The uterotonic effect of vasicine (184) was similar to those of oxytocin and methylergometrine." Vasicine hydrochloride (184 HCl) potentiated the oxytocin-induced contraction of isolated rat and rabbit uterus" and rat mammary gland strips. - The thrombocytopoietic activity of vasicine hydrochloride (184 HCl), its absorption and distribution in mice, its... 

Vasicine hydrochloride (184 HCl) given to pregnant volunteers was well tolerated. Its intraamniotic injection was effective in inducing mid-trimester abortions. ... 

Acetylation of (40) afforded the 3,4-diacetyl derivative, and attempts to further acetylate this product failed to yield a triacetylated product. Passing hydrogen chloride gas through a dry methanolic solution of (40) resulted in the formation of vasicine hydrochloride, indicating dehydration of the tertiary alcohol at C-3 a. Reaction of phosphorus oxychloride with (40) in pyridine yielded chlorodeoxyvasicine. Partial synthesis of (40) was accomplished by heating vasicine and water in a sealed tube at 140—150° for 16 hours. 

Atal CK, Sharma ML, Khajuria A, Kaul A et al. 1982 Thrombopoietic activity of vasicine hydrochloride. Ind J Exp Biol 20 704-709... 

Wakhloo RL, Kaul G, Gupta OP, Atal CK 1980 Safety evaluation in human subjects of vasicine hydrochloride, a promising oxytocic and abortifacient agent. Indian J Pharmacol 12 58A... 

The substance represented by formula (IV), viz., 4-hydroxy-3-allyl-3 4-dihydroqviinazoline, m.p. 130°, was synthesised by Reynolds and Robinson, and proved to be different from vasicine. Spath and Kuffner established the identity of the degradation product (V), upon which formula (IV) for vasicine was chiefly based by synthesis from isatoic anhydride, which, on treatment with glycine ester hydrochloride and sodium meth-oxide, gave the substituted Wppuric acid (VI), and this, on heating with... 

The first total syntheses of 32 were performed by Spath and co-workers (97.98) and by Hanford and Adams (99). Another synthesis was described by Munoz and Madronero (100). From a biogenetic point of view, some syntheses under physiological conditions are very interesting, for example, (1) from 8 -pyrroline and o-aminobenzaldehyde at pH 5 (84,101,102) or (2) from a-keto-8-aminovaleric acid and o-aminobenzaldehyde (103). Compound 32 can also be prepared by reduction of deoxyvasicinone (88,104,137) or by starting from vasicine (via chlorodeoxyvasicine) (105) or from vasicinone (via chlo-rovasicinone) (88). Sattarova et al. (106) reported a method for the quantitative determination of deoxyvasicine hydrochloride. 

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