Synthesis of alkyl catechols and evaluation of their antibacterial and cyfotoxic activity.
A series of potential biologically active mono-, di- and tetra- alkyl catechols were prepared through Friedel- Crafts alkylation of catechol, and evaluated for their antibacterial and cytotoxic activity. The mono-substituted alkyl derivatives showed maximum antibacterial activity in vitro which increased with the increasing length of the alkyl chains. Primary screening results indicated that all the monoalkyl derivatives except 4- (2-octyl) catechol inhibited the growth of B. bronchoseptica and maximum zones of inhibition were observed in case of monohexyl catechols (both n- and 2-hexyl) and monobenzyl derivative. In case of Gram-negative organisms growth of Kl. pneumoniae and A. calcoaceticus was inhibited by several derivatives. Mono-3-octyl-, monononyl- and monobenzyl catechols markedly inhibited the growth of Kl. pneumoniae. Mono-2-heptyl catechol inhibited the growth of six Gram-negative bacteria. Minimum inhibitory concentration of six most active compounds of the series was determined against Gram-positive and Gram-negative organisms; it ranged from < 100 mug/ml to l0 mug/ml. The antibacterial activity of catechol was not significant. Cytotoxicity test done by brine shrimp assays showed that the order of cytotoxicity decreases in going from mono- to tetra- alkyl catechols, and among the mono- alkyl products, a decrease in order of cytotoxicity was noted in going from mono-methyl catechol (LD(50) = 59) to monopentyl catechol (LD(50) = 173) after which the order of cytotoxicity gradually increased upto the largest alkyl substituent tested i.e. monononyl catechol (LD(50) = 114). Methyl and ethyl catechol, which were almost inactive in respect of their antibacterial activity possessed prononounced cytotoxicity as compared to higher homologues. Catechol itself did not show significant cytotoxicity (LD(50) = 393.27).
Siddiqui
B S
BS
H.E.J. Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan.
Adil
Q
Q
Begum
S
S
Siddiqui
S
S
Khan
K A
KA
Khan
S A
SA
Khalid
S M
SM