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AIMS

SYNTHESIS, PHYSICO-CHEMICAL FEATURES AND ANTIMICROBIAL ACTIVITY OF NEW 3 -MERCAPTO- 2 -N-SUBSTITUTED-1,4-NAPHTHOQUINONES. Gabriela Rău 1 , Elena Camelia Stănciulescu 2 , Anca Berbecaru-Iovan 2 , Ana Marina Andrei 2 , Flavia Creţu 2 , Adela Boroghină 3 , Cătălina Gabriela Pisoschi 2.

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AIMS

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  1. SYNTHESIS, PHYSICO-CHEMICAL FEATURES ANDANTIMICROBIAL ACTIVITY OF NEW 3-MERCAPTO-2-N-SUBSTITUTED-1,4-NAPHTHOQUINONES Gabriela Rău1, Elena Camelia Stănciulescu2, Anca Berbecaru-Iovan2, Ana Marina Andrei2, Flavia Creţu2, Adela Boroghină3, Cătălina Gabriela Pisoschi2 1Ist Department of Pharmacy, 2IInd Department of Pharmacy, Faculty of Pharmacy, University of Medicine and PharmacyCraiova, 3Clinical Laboratory, Emergency Clinical County Hospital Craiova AIMS MATERIAL AND METHODS Naphthoquinone and sulfur containing derivatives had been a research subject of much interest due to their antimicrobial, antiviral, anti-inflammatory and antitumor activity. In the present study we describe synthesis, physico-chemical features and antimicrobial activity of new 3-mercapto-2-N-substituted-1,4-naphthoquinones. Reagents and solvents used in the present study were of analytical grade and purchased from Merck and Sigma. Elemental analysis has been made on CHNOS Vario El analyzer. Melting points were measured in open capillary tubes with a Gallenkamp melting point apparatus and are uncorrected. UV-Vis spectra were recorded with a Jasco V-530 spectrophotometer, within the range 200–700 nm on substances solved in DMSO. IR spectra have been recorded in KBr pellets with a BioRad FTS 135 FT-IR spectrophotometer, within the range 3500–400 cm-1. For 1H–NMR spectra a Varian NMR-System 300 spectrometer, at 300 MHz, in CDCl3/DMSO–d6 or DMSO–d6 with TMS as an internal standard was used. Disk diffusion method was used for evaluation of antibacterial activity on Gram-positive and Gram-negative bacterial strains and antifungal activity. RESULTS Several 3-mercapto-2-N-substituted 1,4-naphtoquinones were obtained in a two step synthesis starting from dichlone and appropriate N-substituted amino derivates, then treatment of 2-chloro-3-N-substituted-1,4-naphtoquinones with thiourea (Scheme 1). Crude products were purified by recrystallisation from methanol, purity being verified with chromatography. Yields were between 64-83%. All methods confirmed the structure of compounds and their chemical features are presented behind. Chloro and mercapto derivates were active against Gram-positive bacteria Staphylococcus aureus and had a weak antifungal activity on C. albicans (Table 1). Table 1 Strains Physico-chemical Features 2-chloro-3-(N-thiazol-2-ylamino)-1,4-NQ, 1i - mp. = 164–165oC, yield = 74%; brown powder; IR ν (cm-1): 3249 (w, NH); 1680 (vi, C=O); 1587,793 (m, m, CH aromatic ring); 1H NMR (CDCl3/DMSO–d6): 4.00 (1H, s, NH); 6.56–7.53 (2H, m, CH thiazole); 7.72–8.00 (4H, m, CH aromatic ring); calc. %: C 53.70; H 2.40; Cl 11.01; N 9.63; S 11.01; found, %: C 53.69; H 2.44; Cl 10.98; N 9.60; S 10.98; C13H7N2O2SCl; M = 290.5 g/mol. 4-(2-chloro-3-(N-[4-(1-carboxy-2-hidroxy-phenyl)amino))-1,4-NQ, 2i - mp. = 169.5oC; yield = 83%,; red-brown powder; IR ν (cm-1): 3254 (w, NH); 1679 (vi, C=O); 3618, 1138 (i, OH); 2921, 1718 (m, i, COOH); 1587, 793 (m, m, CH aromatic ring); 1H NMR (CDCl3/DMSO–d6): 3.98 (1H, s, NH); 4.98 (1H, s, OH); 10.96 (1H, s, COOH); 6.16–7.71 (3H, m, CH aromatic ring), 7.75–8.00 (4H, m, CH aromatic ring); calc.%: C 59.38; H 2.91; Cl 10.33;N 4,07; found, %: C 59.40; H2.92; Cl10.30; N4.18; C17H10NO5Cl;M = 343.5 g/mol. 2-mercapto-3-(N-thiazol-2-ylamino)-1,4-NQ, 1p - mp. = 113.5oC; yield = 64%; black powder; IR ν (cm-1): 3239 (w, NH); 1685 (vi, C=O); 2567 (w, SH);1586, 795 (m, m, CH aromatic ring); 1H NMR (DMSO–d6):3.99 (1H, s, NH); 6.56–7.53 (2H, m, CH thiazole); 7.73–8.00 (4H, m, CH aromatic ring); calc. %: C 54.16; H 2.77; N 9.72; S 22.22, found, %: C 54.17; H 2.70;N 9.70; S 22.12; C13H8N2O2S2;M = 288 g/mol. 2-mercapto-3-(N-4-(1-carboxy-2-hidroxy-phenyl)amino))-1,4-NQ, 2p-mp. = 101–102oC; yield = 72%; black powder; IR ν (cm-1): 3256 (w, NH); 1680 (vi, C=O); 2568 (w, SH); 3612, 1209 (i, i, OH); 2922, 1718 (m, i, COOH);1588,794 (m, m, CH aromatic ring); 1H NMR (DMSO–d6): 3.98 (1H, s, NH);1.50 (1H, s, SH); 4.97 (1H, s, OH);10.95 (1H, s, COOH); 6.18–7.71 (3H, m, CH arom. ring).7.74–8.00 (4H, m, CH arom.ring) calc., %: C 59.82; H 3.22; N 4.10; S 9.38; found, %:C 59.85; H 3.13;N 4.00; S 9.30;C17H11NO5S;M = 341 g/mol Scheme 1 CONCLUSIONS These derivates of 1,4-naphthoquinone proved good in vitro antibacterial activity against some Gram positive strains and a weak antifungal effect on C. albicans. This encourages further studies regarding the use of these compounds in antibiotic therapy, design of 1,4-naphthoquinones derivates with improved pharmaceutical properties remaining still a research area of the utmost importance.

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