54293-06-0Relevant articles and documents
TOTAL SYNTHESIS OF THE RACEMIC ALKALOID DIPTOCARPAMINE
Tolstikova, O. V.,Tolstikov, A. G.,Shmakov, V. S.,Galkin, E. G.,Vyrypaev, E. M.,et al.
, p. 199 - 202 (1989)
A route for the synthesis of racemic diptocarpamine from hex-5-enoic acid has been developed.
Evaluation of methylthio-, methylsulfinyl-, and methylsulfonyl- analogs of alkanes and alkanoic acids as cardiac inotropic and antifungal agents
Iqbal, Nadeem,McEwen, Carol-Anne,Sardari, Soroush,Daneshtalab, Mohsen,Knaus, Edward E.
, p. 293 - 298 (2007/10/03)
A group of alkane and alkanoic acid compounds of general formula MeS(O)(m)(CH2)(n)R [m = 0 - 2; n = 1, 5, 13; R = Me, CO2H(Na)] were synthesized for evaluation as cardiac inotropic and antifungal agents. Inotropic activity was determined as the ability of the test compound to modulate in vitro guinea pig atrium contractility. The oxidation state of the S-atom was an important determinant of inotropic modulation since the thio (m = 0) analogs exhibited a positive inotropic effect. In contrast, the sulfonyl (m = 1) and sulfonyl (m = 2) analogs exhibited a negative inotropic effect. A pentyl spacer (n = 5) provided the largest positive or negative inotropic effect. The relative positive, and negative, inotropic potency orders with respect to the R-substituent were Me ≥ CO2H, and CO2Na ≥ Me, respectively. The most potent positive inotrope MeS(CH2)5Me (EC50 = 4.49 x 10-6 M) could serve as a useful lead-compound for the design of a new class of positive inotropic agents. In a broad spectrum antifungal screen, the minimal inhibitory concentration (MIC) range for the five most active compounds was MeSO2(CH2)5Me (0.46-1.83 mM), MeS(CH2)13Me (0.31-1.23 mM), MeSO(CH2)13Me (2(CH2)13Me (0.27-1.09 mM), and MeS(CH2)13CO2H (0.27-1.09 mM), relative to the reference drug Ampotericin B (2)13Me was selective against C. guillermondi, C. neoformans, S. cerevisiae, and A. fumigatus (strain TIMM 1776).
