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Synthesis of 2,3-diarylglutaramides and their antibacterial activity
Abstract
2,3-Diarylglutaramides (4) have been prepared by a one-pot reaction involving hydrolysis of the corresponding diastereomeric (R, R)-glutaronitriles (3) with conc. sulphuric acid at room temperature. Their structure has been established on the basis of their elemental analyses and IR, 1H and 13C NMR spectral data. The antibacterial activity of both 3 and 4 against P .aeruginosa, E. coli, S. aureus and E.faecalis has been determined.
... In this paper we report the effects of a series of 1,2-N,N´-di-(4-R-phenyl)alkanediamides ( Figure 1) (Martinez et al., 2000;Chacon-Garcia and Martinez, 2001;Chacon-Garcia et al., 2003), with strong or partial herbicidal activity against several crops and weeds. Some authors have found that compounds of this type are active against Mycobacterium tuberculosis (Dave et al., 1985), Gram-positive bacteria (Al-Arab et al., 1990), plants (Stauffer, 1975, citotoxic activity (Chacon-Garcia and Martinez, 2001;Chacon-Garcia et al., 2003), Plasmodium spp. (Raynes et al., 1995), inhibiting oxygen evolution in spinach chloroplasts (Kubicoba et al., 1998;, growth and chlorophyll production in Chlorella vulgaris (Kubicova et al., 2000b) and acting as ryanodine receptor modulators (Legocki et al., 2008). ...
Diamides are a class of metabolites that occurring in some Meliaceae plants, in Aglaia spp for example, with an ample body of biological activities, being insecticidal and herbicidal two of the most important. In our program of search for botanical pesticides, a series of N,N ́-di-(4-R-phenyl)-alkanediamides was evaluated for its herbicidal activity. Many of the analogues tested exhibited moderate to good herbicidal activity both pre-emergence and post-emergence and have been found to inhibit energetic metabolism of pre-emergence weeds. The structure-activity relationships were probed by substitution on the benzene ring. Among the variations investigated, it was found that maximal herbicidal activity was obtained by substitution of -F, -CN and -Br at the aromatic portion and by n=2 of the aliphatic long chain. This last number of carbons (n=2) substitution was the key for the inhibitory activity. © 2010 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas.
... In this paper we report the effects of a series of 1,2-N,N´-di-(4-R-phenyl)- alkanediamides (Figure 1) (Martinez et al., 2000; Chacon-Garcia and Martinez, 2001; Chacon-Garcia et al., 2003), with strong or partial herbicidal activity against several crops and weeds. Some authors have found that compounds of this type are active against Mycobacterium tuberculosis (Dave et al., 1985), Gram-positive bacteria (Al-Arab et al., 1990), plants (Stauffer, 1975 ), citotoxic activity (Garcia and Martinez, 2001; Chacon-Garcia et al., 2003), Plasmodium spp. (Raynes et al., 1995), inhibiting oxygen evolution in spinach chloroplasts (Kubicoba et al., 1998;), growth and chlorophyll production in Chlorella vulgaris (Kubicova et al., 2000b) and acting as ryanodine receptor modulators (Legocki et al., 2008). ...
Diamidas son una clase de metabolitos que estan presentes en plantas perteneciente a la familia de la Meliaceas, en Aglaia por ejemplo, poseen un amplio cuerpo de actividades biologicas, siendo la insecticida y la herbicida dos de las mas importantes. En nuestro programa para la busqueda de pesticidas botanicos, una serie de N,N'-di-(4-R-phenyl)-alkanodiamidas se evaluo para su actividad herbicida. Muchos de los analogos exhibieron desde buenas a moderadas actividades, tanto como pre-emergentes como post-emergentes y ademas se encontro que inhiben el metabolismo pre-emergente energetico de malezas. La relacion estructura-actividad fue probada por sustitución sobre al anillo aromatico. Entre las variaciones investigadas, se encontro que la maxima actividad herbicida se obtuvo por sustitución de F, CN y Br en la porcion aromatica y por n=2 del largo de la cadena alifatica. Este ultimo numero de carbonos de sustitución (n=2) fue clave para la actividad inhibitoria.
... Other authors have described various kinds of biological activity of alkanediamide derivatives as well. For example, some 2-methylcarbonylbutanediamides are active against M. tuberculosis [2], 2,3diarylpentanediamides display activity against Gram-positive bacteria [3], and N,N'-substituted 2halobutanediamides act as herbicides [4]. Raynes et al. studied the influence of the length of the connecting chain on the antimalarial activity of bisquinolines; the derivative of butanediamide was the most efficient [5]. ...
A set of N,N'-diarylalkanediamides was synthesized. The compounds were tested for their antimycobacterial and antialgal activity. The antimycobacterial activity of N,N'-diarylalkanediamides depends on the lipophilicity of the respective acid. Antimycobacterially active substances were found only in the series of N,N'-diarylethanediamides and N,N'-diarylbutanediamides. Other compounds (derivatives of pentane-, hexane-, octane- and nonanediamide) were inactive against various strains of mycobacteria. The compounds inhibited growth and chlorophyll production in Chlorella vulgaris. Their relatively low antialgal activity is probably connected with their lowered aqueous solubility, and hence by a restricted passage of the inhibitor through the hydrophilic regions of thylakoid membranes.
A set of twelve new N,N'-diphenylalkanediamides was prepared by the reactions of acyl chlorides with appropriate anilines. The inhibition of oxygen evolution rate (OER) in spinach chloroplasts by the synthesized compounds was investigated. With the exception of N,N'-bis(3,4-dichlorophenyl)butanediamide (IC50 = 22 μmol dm-3), the other studied derivatives of N,N'-diphenylbutanediamide did not affect photosynthetic activity of spinach chloroplasts. The OER-inhibiting activity of N,N'-bis(3,4-dichlorophenyl)alkanediamides (alkane = butane, pentane, hexane, octane, nonane) showed a linear decrease with increasing lipophilicity of the studied compounds.
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