Chemical transformations of antibiotic X-537A and their effect on antibacterial activity

Abstract

chloropropiono-2',6'-xylidide (7.0 g, 0.033 mol), tis-octahydro-1//pyrindine HC1 (3.75 g, 0.03 mol), Na2C03 (7.5 g, 0.06 mol), and KI (0.1 g) in 4-methyl-2-pentanone (250 ml) was stirred and refluxed for 72 hr. After cooling, H20 was added. The organic layer was separated and dried (MgS04), and the solvent was removed in vacuo.The oily residue was converted into its HC1 salt in z-Pr20-HCl.Crystallization from z-Pr20-z-PrOH gave pure 11 (7.27 g, 72%), mp 202-203°. Anal. (C19H28N20'HC1) C, , 4,4a,5,6,7,8,(2//)-quinolinepropiono-2 ',6 -xylidide Hydrochloride (21). A suspension of 3chloropropiono-2',6'-xylidide (7.0 g, 0.033 mol), ds-decahydroquinoline HC1 (5.27 g, 0.03 mol), and NaHC03 (8.4 g, 0.1 mol) in EtOH (200 ml) was stirred and refluxed overnight. After cooling the mixture was concentrated in vacuo and 2 N aqueous HC1 was added.

Ionophore–Phospholipid Interactions in Langmuir Films in Relation to Ionophore Selectivity toward Plasmodium-Infected Erythrocytes

“…Monensin A, nigericin, narasin A, lonomycin A, and lasalocid A and its derivative, 5-bromo lasalocid A, were stock samples from the Laboratoire de Chimie Organique Biologique, CNRS URA 485 (Aubière, France). 5-Bromo lasalocid A was obtained by hemisynthesis as described previously (8). RPMI 1640 was obtained from Gibco Lab (France).…”

Permeability of lipid bilayer membranes to biogenic amines and cations: Changes induced by ionophores and correlations with biological activities

“…3), whereas Ro 20-0083 increased a unselectively with respect to undoped lipid bilayers by a factor of 100 (the factors refer to an antibiotic concentration of 0.07 %). Columns BE and BTA show the relative in vitro activity (growth inhibition) of the antibiotics vs. bacillus E and bacillus TA as reported by J. W. Westley et aL [24]. Ro 20-0006 increased G with no preference for the same ions by a factor of 100 whereas a(K +) increased by a factor of 1,000.…”

“…amount of NE after time t, one gets [1,23] where p = permeability coefficient of NE. Columns BE and BTA show the relative in vitro antibacterial activities [24] against bacillus E and bacillus TA; column C refers to the coccidiostatic activity (as in Table 1). The permeability coefficients p (cm sec-1) for NE were determined from the measurements in Fig.…”

“…It was isolated [2] in 1951 and its structure was analyzed [6] in 1970. Various interesting biological activities of Ro 2-2985 were reported [8,10,17,20,21,24] within the last few years especially in cardiotonic actions [3, i0, 16, 17, 21]. Recently, it was found that Ro 2-2985 has not only ionophoric properties but also enhances the permeation of catecholamines in biological membranes [10] as well as in bulk organic phases [17].…”

Spectrofluorometric Determination of the Antibiotic Lasalocid in Blood

“…Studies pertaining to the structure elucidation (3)(4)(5) and the biosynthesis (6)(7)(8) of the compound were reported. Other investigations have dealt with chemical transformations and their effects on antibacterial activity (9), nitration (lo), and pyrolytic cleavage (11).…”