Synthesis and antimuscarinic activity of some 1-cycloalkyl-1-hydroxy-1-phenyl-3-(4-substituted piperazinyl)-2-propanones and related compounds was written by Kaiser, Carl;Audia, Vicki H.;Carter, J. Paul;McPherson, Daniel W.;Waid, Philip P.;Lowe, Valerie C.;Noronha-Blob, Lalita. And the article was included in Journal of Medicinal Chemistry in 1993.COA of Formula: C7H16N2 This article mentions the following:
A new class of substituted 1-phenyl-3-piperazinyl-2-propanones I (R = cyclobutyl, cyclohexyl, iso-Bu, cyclopropyl, Ph, cyclopentyl, R1 = H, Me, CH2CCH, CH2Ph, CH2CN, CH2C6H4NO2-4, etc.) and PhCR(OH)COCH2R2 [II, R = cyclopropyl, cyclobutyl, cyclopentyl, Ph, R2 = 4-hydroxy-1-piperidinyl, 4-(1-pyrrolidinyl)piperidinyl, NH(CH2)2NMe2) with antimuscarinic activity were prepared Thus, PhCR(OH)COMe were brominated to give PhCR(OH)COCH2Br which were aminated to give I and II. As part of a structure-activity relationship study of this class, various structural modifications, particularly one involving substitution of position 1 and the terminal piperazine nitrogen, were investigated. The objective of this study was to derive new antimuscarinic agents with potential utility in treating urinary incontinence associated with bladder muscle instability. These compounds were examined for M1, M2, and M3 muscarinic receptor selectivity in isolated tissue assay and for in vivo effects on urinary bladder contraction, mydriasis, and salivation in guinea pigs. Potency and selectivity in these assays were influenced most notably by the nature of the substituent group on the terminal nitrogen of the piperazine moiety. Benzyl substitution was particularly advantageous in producing compounds with functional M3 receptor (smooth muscle) and bladder selectivity; it provided several candidates for clin. study. In vivo, I (R = cyclobutyl, R1 = CH2Ph) demonstrated 11- and 37-fold separations in its effect on bladder function vs. mydriatic and salivation responses, resp. The corresponding 2-chlorobenzyl derivative was more than 178-fold selective for M3 vs. M1 and M2 muscarinic receptors. I (R = Ph, R1 = CH2Ph) was 18-fold selective for M3 vs. M1 and 242-fold selective for M3 vs. M2 receptors. It was also selective in guinea pigs, where it displayed 20- and 41-fold separations between bladder function and effect on mydriasis and salivation, resp. In general, the results of this study are consistent with the proposition that the described piperazinylpropanones interact with muscarinic receptors in a hydrogen-bonded form that presents a conformation similar to that apparently adopted by classical antimuscarinic agents. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1COA of Formula: C7H16N2).
1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine belongs to the family of medicines called anthelmintics. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. COA of Formula: C7H16N2
Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics