3α-Hydroxy-3β-(phenylethynyl)-5β-pregnan-20-ones: Synthesis and Pharmacological Activity of Neuroactive Steroids with High Affinity for GABAA Receptors was written by Upasani, Ravindra B.;Yang, Kevin C.;Acosta-Burruel, Manuel;Konkoy, Chris S.;McLellan, James A.;Woodward, Richard M.;Lan, Nancy C.;Carter, Richard B.;Hawkinson, Jon E.. And the article was included in Journal of Medicinal Chemistry in 1997.Application of 77350-52-8 This article mentions the following:
Neuroactive steroids that allosterically modulate GABAA receptors have potential uses as anticonvulsants, anxiolytics, and sedative-hypnotic agents. Recently, a series of pregnanes substituted with simple alkyl groups at the 3β-position were synthesized and found to be active in vitro. The present report describes the synthesis of a series of substituted 3α-hydroxy-3β-(phenylethynyl)pregnan-20-ones I [R = 4-MeO, 4-Cl, 4-Me2N, CN-4, CONH2-4, 4-Ph, 4-HO, 4-O2N, 2-MeO, 3,4-(MeO)2, 3,4-OCH2O, 2-HO, 3-HO, 4-Me, 4-H2N, 4-CF3, 4-Ac, 4-EtO2C, CHO-4, CONEt2-4, COPh-4; R1 = Me; R = Ac, CO2Et-4, R1 = H] and their in vitro structure-activity relationship determined by their potency for inhibition of [35S]TBPS binding in rat brain membranes. Appropriate substitution of the Ph group results in ligands with particularly high affinity for the neuroactive steroid site on GABAA receptors [e.g., I (R = 4-Ac; R1 = Me), IC50 10 nM]. The potency of selected steroids was confirmed electrophysiol. in oocytes expressing cloned human GABAA α1β2γ2L receptors [e.g., I (R = 4-Ac; R1 = Me), EC50 6.6 nM]. Consistent with their in vitro activity, some of the 3β-(phenylethynyl)-substituted steroids displayed anticonvulsant activity in the pentylenetetrazol (PTZ) and maximal electroshock (MES) tests following i.p. administration in mice. Notably, the 3β-[(4-acetylphenyl)ethynyl]-19-nor derivative I (R = Ac, R1 = H) provided an attractive anticonvulsant profile (PTZ and MES ED50 values of 2.8 and 9.2 mg/kg, resp.). A new pharmacophore for the neuroactive steroid site of GABAA receptors is proposed based upon the high affinity of certain substituted 3β-(phenylethynyl) steroids. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Application of 77350-52-8).
N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Application of 77350-52-8
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com