The Reaction Of Some Amino Acids In The Diffrent Aromatic Compounds And Synthesis Of Derivatives With Expected Biological Activites :

Shafey Donia. 

Several~ 3,5-dinitro benzoyl amino acids were readilyprep&~ed by direct reaction of 3,5-dinitro benzoyl chloride( Xlll ) with the appropriate amino acids in dioxane-Et3Nmixture. Coupling reaction with L-, B-and DL-alanine, L-andDL-Serine, L-leucine, L-and Dl-phenyl alanine and L_tyrosineneeded 1 : 1.2 mole of the .acid chloride ( ( Xlll ) and theamino aci d respec tivily ( Xl V - XXll ).( XlV ) , A = L - Ala •, ( XU ) , A = L - Leu( XV ) , A = B - Ala •, ( XX ) , A = L - Phe( XVl ) , A = DL - f.la •, ( XXl ) , A = DL - Phe( zvn.) , A ••L - Ser ; ( XXll) ,A=L-Tyr( xvin.), A = DL - SerSyn~hesis of 3,5 dinitro benzoyl amino acid methylesters ( XXlll _ XXX IV)were successively performed bycoupling 3,5 _ dinitro benzoyl chloride ( Xlll ) with theappropriate amino acid methyl esters in dioxane - EtJNmedium.-11-( zxua ) , A = Gly - OMe •• ( XXlX ) , A = DL - Val-Ollie( XXlV ) , A = L - Ala - OMe,( XXX ) , ll. = L- - Leu-OMe( XXV ) , .4 = B - I.la - OMe,( XXXl ) , A = DL-nor-Leu-CMe( XXVl ) , /l. = L - Ser - OMe,(XXXll ) , I, = DL-Phe-OMe( XXVII ) • A = DL-Ser- OMe • (XXXlll) , A = L-tyr - OMe( XXVlll) , A = L-Val - OMe , (XXXlV ) ,A=L-Tryp-OMelrepQration.of the hydrazides ( XXXV- XLIII) wereeasily performed by the action of hydrazine hydrate on thec~~reeponding methyl esters in ethanol.o~~ )- co~ _~ _ COBHEH~o N (2 R( XXXV- XLlll )( XXXV) , A = L - Ala - N2 HJ ; (XL ) A = L-Leu-N2HJ( XXXVI) , A = B - Ala •.. N2 HJ ; ( XLI ) A= Dl-nor-Leu-N2HJ( XXXVII), I. ””L - Ser - N2H3 ; ( XLll) A = L-Tyr-N2H3(XXXVIll), f. = L - Val - N2H3 ; ( XLlll)A =. L-Tryp- n2H3(XXXIX ), A = DL-Val-n2H3-----.- - _._----------------- ),11 -Coupl~ng of some J,5-dinitro benzoyl amino acidswith different amino acid methyl esters in tetrahydroturan-EtJ~ using the dicyclohexylcarbodiimide method afforded thedipeptide~ ( XLIV - Llll ).02No- ’I ’ CO;1H - CH - ,°2N R(XLIV -A• •-eONH-eHIR’- COOCHJL11l )( L,lV ) , A = L - Ala DL - Val - OMe( XLV ) , 1l. = L - .Ha DL - Phe - OMe( XLVl ) , A = Dl.- l.la DL - Val - OMe( XLVll) t A = L - Ser - L - Val - OMe( XLV HI),A = L - Ser DL - Phe - OMe(XLU) t A = L - Fhe DL - Val - OMe( L ) t A = L -Tyr DL - Ser - OMe( LI ) t A = L -Tyr DL - Val - OMe( L11 ) t 1. =L -Tyr DL - nor - Leu - OMe( LUI ) I A = L - Tyr DL - Phe - OMeThe biological activities of all the synthesizedJ,5-dinitro benzoyl amino acids, esters, hyd~Qzides anddipeptide esters ( XlV - Llll ) were tested againstdifferent gram - Positive, gram-megative microorganismsand fungi. Some of the synthesized amino acid derivativeswere found to possess different ”biological activities.