Some derivatives of 2'-formylbiphenyl-2-carboxylic acid as potential bactericides
Abstract Generated abstract
This paper reports the synthesis and preliminary biological evaluation of semicarbazones derived from 2'-formylbiphenyl-2-carboxylic acid and several of its esters as potential bactericidal agents. The compounds were prepared by reacting the acid or ester substrates with semicarbazide hydrochloride in alkaline alcoholic solution, yielding eight previously undescribed products characterized by melting point, empirical formula, and nitrogen analysis. Testing at the Kiev Institute of Tuberculosis indicated that all synthesized compounds inhibited the growth of Mycobacterium tuberculosis, with the n-butyl and iso-butyl ester semicarbazones showing the greatest activity at the highest dilution examined. The results suggest that antimycobacterial activity in this series increases with increasing molecular weight.
Full Text
Some Derivatives of $2'$-Formyldiphenyl-2-carboxylic Acid as Potential Bactericides
I. L. Khalfina
(Presented by the scientific seminar of the departments and laboratories of organic synthesis)
We have obtained a series of oximes and thiosemicarbazones of $2'$-formyldiphenyl-2-carboxylic acid. Some of the compounds obtained proved to be good fungicides. According to patent data, many semicarbazones of aldehydes and ketones possess high fungicidal and bactericidal properties [1–3].
It seemed of interest to synthesize a series of semicarbazones of $2'$-formyldiphenyl-2-carboxylic acid and some of its esters and to test their bactericidal activity. The synthesis of these compounds was carried out by the interaction of $2'$-formyldiphenyl-2-carboxylic acid and its esters with hydrochloric semicarbazide in the presence of caustic soda. In this way eight compounds not described in the literature were obtained.
Table
| No. | R | Yield, % | M.p., °C | Empirical formula | Nitrogen, %, found | Nitrogen, %, calculated |
|---|---|---|---|---|---|---|
| 1 | H | 92 | 198–199 | $\mathrm{C_{15}H_{13}O_3N_3}$ | 15.10 | 14.84 |
| 2 | $\mathrm{CH_3}$ | 95 | 145–146 | $\mathrm{C_{16}H_{15}O_3N_3}$ | 14.33 | 14.14 |
| 3 | $\mathrm{C_2H_5}$ | 92 | 131–132 | $\mathrm{C_{17}H_{17}O_3N_3}$ | 13.76 | 13.50 |
| 4 | $n$-$\mathrm{C_3H_7}$ | 92 | 121–122 | $\mathrm{C_{18}H_{19}O_3N_3}$ | 12.89 | 12.92 |
| 5 | iso-$\mathrm{C_3H_7}$ | 91 | 112–112 | $\mathrm{C_{18}H_{19}O_3N_3}$ | 12.68 | 12.92 |
| 6 | $n$-$\mathrm{C_4H_9}$ | 90 | 94–95 | $\mathrm{C_{19}H_{21}O_3N_3}$ | 12.45 | 12.39 |
| 7 | iso-$\mathrm{C_4H_9}$ | 90 | 135–137 | $\mathrm{C_{19}H_{21}O_3N_3}$ | 12.75 | 12.99 |
| 8 | $n$-$\mathrm{C_5H_{11}}$ | 90 | 96–98 | $\mathrm{C_{20}H_{23}O_3N_3}$ | 11.74 | 11.80 |
The study of the bactericidal properties of the compounds obtained was carried out at the Kiev Institute of Tuberculosis under the direction of Professor R. O. Drabkina. The tests showed that all the compounds obtained by us inhibit the growth of tuberculosis mycobacteria; the most active proved to be the semicarbazones of the $n$- and iso-butyl esters of $2'$-formyldiphenyl-2-carboxylic acid: they inhibited the growth of myco-
tuberculosis bacteria at a dilution of 1:320000 (higher dilutions were not tested); with increasing molecular weight of the semicarbazones, the activity against Mycobacterium tuberculosis increases.
Experimental Part
\(2^1\)-Formyldiphenyl-2-carboxylic acid was obtained from technical-grade phenanthrene and had m.p. 130–132°.
All the compounds listed in the table were obtained under the following conditions: 10 g (0.044 g-mole) of \(2^1\)-formyldiphenyl-2-carboxylic acid or its ester, 5 g (0.044 g/mole) of semicarbazide hydrochloride, 16.2 ml of 10% sodium hydroxide solution, and 25 ml of alcohol were heated for two hours. After cooling, a white substance precipitated from the reaction mixture. The products were recrystallized from 40% ethanol. Some properties of the compounds obtained are given in the table.
REFERENCES
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