Printer Friendly

Synthesis, characterization and biological activities of some new acid hydrazones derived from ethyl-2-[(N-benzoyl) 2,3-dichloroanilido] acetohydrazide.

Introduction

Hydrazones possessing an azometine -NHN = CH- Proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. Acid hydrazides have frequently been investigated for testing their potentiality as tuberculostats [1-8]. Hydrazides and their condensation products have displayed diverse range of biological properties such as bacteriocidal [9-10], anti fungal [11], anti-convulsant [12-15], anti-helmintic [16], anti-tumor [17-20], anti-leprotic [21], anti malerial [22-23], anti-cancer [24-31], anti-depressant [32], anti-HIV [33], analgesic-antiinflammatory [34], leishmanicidal [35], vasodilator activities [36].

Experimental

All chemicals used were of A.R. grade (either of B.D.H. or Excel-R or Extra pure E. Merk quality). The structures of the compounds were determined by elemental analysis, IR and NMR spectral data. IR spectra (KBr) are recorded on a Perkin-Elmer 283 spectrophotometer. NMR spectra (CD[Cl.sub.3]) are recorded on Varian EM 360 L spectrophotometer. Melting points of the compounds are determined in open capillary tubes and are uncorrected. Purity of the compounds is checked on T.L.C. using Silica Gel-G. Elemental analysis is performed on Carlo-Erba 1108 analyser.

Synthesis of Ethyl-2-[2, 3-dichloroanilido] Ethanoate [1]:

A mixture of 2, 3-dichloroaniline (10ml) and diethylmalonate (20ml) was refluxed for forty five minutes in a round bottomed flask fitted with an air condenser of such a length (14") that ethanol formed escaped and diethylmalonate flowed back into the flask. Contents were cooled, ethanol (30 ml) was added, when malon-2,3 dichlorodianilide separated out. It was filtered under suction. The filtrate was poured on to crushed ice (Ca160g) and stirred when ethyl-2-(2, 3-dichloroanilido) ethanoate precipitated as green mass. On recrystallization from aqueous ethanol (50%), ester was obtained as white crystals. Yield: 81%, M. P.: 88[degrees]C, M. W.: 276. Anal. calculation for [C.sub.11], [H.sub.11], [N.sub.11], [O.sub.3] [Cl.sub.2]: Found: C 39.20, H: 03.24, O: 14.25, N: 4.14, Cl: 21.09, Calcd. C: 39.21, H: 03.26, O: 14.26, N: 04.15, Cl: 21.16.

IR [KBr] [V.sub.max] [Cm.sup.-1]: 1665-1660 [C = O diketone], 1290 [-C-O- Ester], 760-755 [2,3 disubstituted benzene], 1250 [C-Cl Stretching], 1590, 1520, 1440 [C = C Ring stretching], 3150 [N-H Stretching], 3040[C-H aromatic], 1330-1322 [C-H Stretching].

PMR (DMSO): [delta] 4.42 (2H, s, CO-C[H.sub.2]-CO), 4.0 (2H, s, N[H.sub.2]), 7.4-8.6 (3H, m, Ar-H), 9.2 (1H, s, CO-NH [D.sub.2]O exchangeable), 10.6 [1H, s, Ar-NH [D.sub.2]O exchangeable].

Synthesis of Ethyl-2-[(N-benzoyl) 2, 3-dichloroanilido] ethanoate [2]:

Benzoyl chloride (8.46 gm; 0.06 mol), dioxane (6 ml), Ethyl-2-(2,3-dichloroanilido) ethanoate (16.5 gm; 0.06 mol) and Triethylamine (6.06 gm; 0.06 mol) were placed in a round bottomed flask carrying reflux condensor having calcium chloride guard tube. The contents were heated on a boiling water bath for two hours and kept over night when triethylamine hydrochloride separated. It was filtered under suction and the filtrate was poured on to crushed ice (Ca180 g) and stirred when Ethyl-2-[(N-benzoyl) 2, 3-dichloroanilido]ethanoate separated or solid. It was filtered under suction, dried and purified by recrystallisation from aqueous methanol (1:1) in white crystals.

Yield = 78.4 %, MP = 94[degrees]C

Analytical calculation for [C.sub.18][H.sub.15][N.sub.1][O.sub.4][Cl.sub.2]: [FW = 380], Calculated: N 02.95, C 45.64, H 03.38, O 13.50, Cl 15.00, Found: N 02.94, C 45.62, H 03.37, O 13.52, Cl 15.02.

IR [KBr] [V.sub.max] [cm.sup.-1]: 1720 [C = O diketone], 1300 [-C-O- Ester], 762[2,3-disubstituted benzene], 1090 [C-Cl Stretching], 1590, 1520, 1440 [C=C Ring stretching], 3160 [N-H Stretching], 3040[C-H aromatic], 1330-1322 [C-H Stretching].

PMR (DMSO): [delta] 4.44 [2H, s, CO-C[H.sub.2]-CO], 4.1 [2H, s, N[H.sub.2]], 7.2-8.5 [3H, m, Ar-H], 9.4 [1H, s, CO-NH [D.sub.2]O exchangeable], 10.8 [1H, s, Ar-NH [D.sub.2]O exchangeable].

Synthesis of Ethyl-2-[(N-benzoyl) 2, 3-dichloroanilido] acetohydrazide [3]: Ethyl-2-[(N-benzoyl) 2, 3-dichloroanilido]ethanoate (10.98 gm; 0.03 mol), ethanol (8 ml) and hydrazine hydrate (15 ml; 70%) were mixed together and stirred for thirty five minutes. Ethyl-2-[(N-benzoyl) 2, 3-dichloroanilido] acetohydrazide was filtered under suction and recrystallised from ethanol in white crystals.

Yield; 76%, MP = 172[degrees]C, MW 366

Analytical calculation for [C.sub.16] [H.sub.13] [N.sub.3] [O.sub.3] [Cl.sub.2]: Calculated: N 09.04, C 41.32, H 03.01, O 10.33, Cl 15.28, Found: N 09.01, C 41.30, H 03.00, O 10.31, Cl 15.27.

IR [KBr] [V.sub.max] [cm.sup.-1]: 3160 [N-H Stretching], 3048 [C-H aromatic], 1660 [C = O diketone], 1432 [C-Cl aromatic], 1595, 1520, 1445 [C = C ring stretching].

PMR (DMSO): [delta] 4.44 (2H, s, CO-C[H.sub.2]-CO), 4.1 (2H, s, N[H.sub.2]), 7.2-8.5 (3H, m, Ar-H), 9.4 (1H, s, CO-NH [D.sub.2]O exchangeable), 10.9 (1H, s, Ar-NH [D.sub.2]O exchangeable)

Synthesis of Ethyl-2-[(N-benzoyl) 2, 3-dichloroanilido]acetohydrazone [4]:

Ethyl-2-[(N-benzoyl) 2, 3-dichloroanilido]acetohydrazide (0.001 mol) and (0.001 mol) of aromatic aldehyde or ketone dissolve in absolute alcohol and added 2-drops of conc. [H.sub.2]S[O.sub.4] and stirred for 15 minutes. It was filtered under suction and recrystallised from hot ethanol.

M.F. [C.sub.23][H.sub.18][O.sub.3][N.sub.3][Cl.sub.2], Colour: White, Yield: 91%, M.P = 216 [degrees]C, F.W: 455,

Analytical calculation for [C.sub.23][H.sub.18][O.sub.3][N.sub.3][Cl.sub.2] Calculated: N 12.04, C 54.85, H 03.71, O 09.14, Cl 20.28, Found: N 11.99, C 54.83, H 03.70, O 10.31, Cl 20.25.

IR Absorption band ([cm.sup.-1]): 3150 (N-H stretching), 2960-2970 (C-H aliphatic), 1662-1660 (C = O Ketone), 785-778 (C-Cl Stretching), 760 (2, 3-disubstituted benzene).

NMR Spectra: ([delta] DMSO), 2.25(2 H, s, CH2), 4.21(1 H, s, NH), 6.95-7.2 (10 H, m, ArH. Synthetic strategy has been out lined in scheme-I. Mechanism for the formation of acid hydrazones is given in chart-I.

[FORMULA EXPRESSION NOT REPRODUCIBLE IN ASCII]

[FORMULA EXPRESSION NOT REPRODUCIBLE IN ASCII]

Biological Evaluation

Anti-bacterial activity

Newly synthesized compounds (1, 2, 3, 4, 5, 6, 7, 8, 9,12,13,14,15,16 and 17) have been tested for their antibacterial activity against gram positive bacteria S. albus, S. aureus and gram negative bacteria E. Coli and Pseudomonas piosineus by agar plate disc diffusion method at 30 [micro]g/mL concentration. Ampicillin and tetracycline were used as a reference compounds. The compound 1, 3, 4, 12, 13, 14 and 15 shown significant activities and compound 2, 5, 6, 7, 8, 9, 16 and 17 have shown moderate activity.

Anti-fungal activity

The same compounds were tested for their antifungal activity against Candida albicans, Aspergillus niger and Alternaria alternata at concentration of 30 mg/ml using sabouraud dextrose agar media. The compound 1, 4, 12, 13, 14 and15 shown significant activity and compound 2, 5, 8, 9, 16 and 17 have shown moderate activity against Candida albicans and Aspergillus niger. All the other compounds did not show significant activity against the fungi at the concentration used.

Tuberculostatic Activity:

Some new compounds have been tested for antitubercular activity in-vitro using Mycobacterium tuberculosis. The compounds were incorporated into Lowenstein Jensen egg medium having concentrations of 10 and 100 mg/ml and were inoculated with Mycobacterium tuberculosis, [H.sub.27] Rv strains, incubated at 37[degrees]C and observed weekly for the growth of organism for eight weeks. Ethyl-2-[(N-benzoyl)2,3dichloroanilido] acetohydrazide, Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of 4-N,N-Bis 2' cyanoethylamino benzaldehyde and Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of acetophenone inhibited the growth of Mycobacterium tuberculosis at 100mg/ml concentration other compounds were found to be inactive. Results are assembled in table-II.

Results and Discussion

New acidhydrazones have been synthesised by the reaction of Ethyl-2 [(N-benzoyl) 2, 3-dichloroanilido]acetohydrazide with various Carbonyl Compounds in 38 to 92% yield. Hydrazones are white, brown and yellow colour solids, having high melting points. The structure of all the compounds are confirmed by IR, PMR, and Mass spectral data and are further supported by correct elemental analysis. Newly synthesized compounds (1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 13, 14, 15, 16 and 17) have been tested for their antibacterial activity against gram positive bacteria S. albus, S. aureus and gram negative bacteria E. Coli and Pseudomonas piosineus. The compound 1, 3, 4, 12, 13, 14 and 15 shown significant activities and compound 2, 5, 6, 7, 8, 9, 16 and 17 have shown moderate activity. The same compounds were tested for their antifungal activity against Candida albicans, Aspergillus niger and Alternaria alternata at concentration of 30 mg/mL using sabouraud dextrose agar media. The compound 1, 4, 12, 13, 14 and15 shown significant activity and compound 2, 5, 8, 9, 16 and 17 have shown moderate activity against Candida albicans and Aspergillus niger. All the other compounds did not show significant activity against the fungi at the concentration used. The same compounds were tested for their antitubercular activity against Mycobacterium tuberculosis. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazide, Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of 4-N,N-Bis 2' cyanoethylamino benzaldehyde and Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of acetophenone inhibited the growth of Mycobacterium tuberculosis at 100mg/ml concentration other compounds were found to be inactive .

Conclusion

Newly synthesized compounds (1, 2, 3, 4, 5, 6, 7, 8, 9,12,13,14,15,16 and 17) have been tested for their antibacterial activity against gram positive bacteria S. albus, S. aureus and gram negative bacteria E. Coli and Pseudomonas piosineus by agar plate disc diffusion method at 30 [micro]g/mL concentration. Ampicillin and tetracycline were used as a reference compounds. The compound 1, 3, 4, 12, 13, 14 and 15 shown significant activity and compound 2, 5, 6, 7, 8, 9, 16 and 17 have shown moderate activity. The same compounds were tested for their antifungal activity against Candida albicans, Aspergillus niger and Alternaria alternata at concentration of 30 mg/mL using sabouraud dextrose agar media. The compound 1, 4, 12, 13, 14 and 15 shown significant activity and compound 2, 5, 8, 9, 16 and 17 have shown moderate activity against Candida albicans and Aspergillus niger. All the other compounds did not show significant activity against the fungi at the concentration used. The same compounds were tested for their antitubercular activity against Mycobacterium tuberculosis. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazide, Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of 4-N,N-Bis 2' cyanoethylamino benzaldehyde and Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of acetophenone inhibited the growth of Mycobacterium tuberculosis at 100mg/mL concentration other compounds were found to be inactive .

Acknowledgement

The authors are thankful to Director, C. D. R. I. Lucknow (U. P.), for elemental analysis, Director, Tuberculosis Research Centre, Amargadh (Gujrat), for testing tuberculostatic activity and Director, D. R. D. E. Gwalior (M.P.), for spectral studies, and Director, Cancer Hospital and Research Institute, Gwalior (M. P.), for Biological activities. We are also grateful to principal SMS Government Model Science College, Gwalior (M.P), for providing research facilities.

References

[1] Buu-Hoi, Rene Royer, J. J. Jouin, J. Lecocq and D. Guettier, Bull. Soc. Chim., France, 128-36 (1947).

[2] Shichiro, Kakimoto and Kenichi Yamamoto; J. Pharm. Soc. Japan, 74, 997-9 (1954); C. A. Vol. 49, 11650 g (1955).

[3] L. Stoicescu-Crivetz and L. Mandasescu, Acad. rep. populare Romine, Studii, Cercetare, Chim. 4, 175-82 (1956); C.A. Vol. 51, 10421 h (1957).

[4] Agarwal S. K., Chandra R., Gupta R., Tutlani D. R.; J. Inst. Chem. (India), 59 (5) 225 (1987); C.A. Vol. 108, 164594 w (1988).

[5] Swiss 419, 139 (1967); C.A. Vol. 68, 29709 C (1968).

[6] R. Cavier and R. Rips (Fac. Pharm, Paris), J. Med. Chem 8 (5), 706-8 (1965).

[7] Martynovskii A. A., Samura B.A. and Co-workers, Med. Inst. Zaporzne, USSR, Khim. Farm. Zh. 24 (7), 31-2 (1990), C.A. Vol. 113, 164948 t (1990).

[8] Strokin, Yu. V, Karasovskii, I.A. and co-workers, (Bashk. Med.Inst., UFA, USSR), Khim.Farm. Zh, 24 (7) 45-8 (1990), C.A. Vol. 114,172 e, (1991).

[9] Gardner, T.S.; Wenis, E.; and Lee, J.; J. Org. Chem., 26, 1514 (1961).

[10] Willy, R.H.; Slaymaker, S.; and Krans H.; J. Org. Chem. 22, 204 (1957).

[11] Omar, A.; Mohsen, M.E.; Farghaly, A.M.; Hazzai, A.A.B.; Eshba, N.H. (Fac. Pharm. Univ. Alexandria, Egypt). Pharmazie (1980); C.A., Vol. 95, 25382 a (1981).

[12] Bhat, A.K.; Bhamaria, R.P.; Patel, M.R.; Bellare, R.A.; and Deliwalia, C.V.; Indian J. Chem. 10, 694 (1972).

[13] Rollas, S.; Kucukguzel, S. G.; Molecules 12, 1910-1939, (2007).

[14] Rollas S.; Gulerman, N.; Erdeniz, H; Farmaco 57, 17, (2002).

[15] Kaymakcioglu K.B.; Oruc, E.E.; Unsalan, S.; Kandemirli,F.; Shvets, N.; Rollas, S.; Anatholy, D.; Eur. J. Med. Chem. 41, 1253-1261, (2006).

[16] Kalsi, R.; Shrimali, M.; Bhalla, T. N.; Barthwal, J. P.; Indian J. Pharm. Sci. 41, 353-359, (2006).

[17] Ragavendran, J.; Sriram,D.; Patel,S.; Reddy,I.; Bharathwajan,N.; Stables, J.; yogeeswari,P.; Eur. J. Med. Chem. 42,146-151, (2007).

[18] Salgin-Goksen, U.; Gokhan-Kelekci, N.; Goktas, O.; Koysal, Y.; Kilic, E.; Isik, S.; Aktay,G.; Ozalp, M.; Bioorg. Med. Chem.15, 5738-5751, (2007).

[19] Kucukguzel, S.G.; Mazi, A.; Sahin, F.; Ozturk S.; Stables, J.P.; Eur. J. Med. Chem. 38, 1005-1009, (2003).

[20] Loncle, C.; Brunel, J.; Vidal, N.; Dherbomez, M.; Letourneux, Y.; Eur. J. Med. Chem. 39, 1067-1071, (2004).

[21] Masunari, A.; Tavares, L.C.; Bioorg. Med. Chem.15, 4229-4236, (2007).

[22] Sriram, D.; Yogeeswari, P.; Madhu, K.; Bioorg. Med. Chem. Lett. 15, 4502 4505, (2005).

[23] Bijev, A.; Lett.Drug Des. Discov, 03, 506-512, (2006).

[24] Nayyar, A.; Jain, R.; Med. Chem. 12, 1873-1886, (2005).

[25] Scior, T.; Garces-Eisele, S.J.; Curr.Med. Chem.13, 2205-2219, (2006).

[26] Janin, Y.; Bioorg. Med.Chem.15, 2479-2513, (2007).

[27] Ulusoy, N.; Gursoy, A.; Otuk, G.; Kiraz, M. Farmaco 56, 947-952, (2001).

[28] Linhong j, Jiang C, Baoan S, Zhuo C, Song Y, Qianzhu L, Deyu H and Ruiqing X, Bioorg Med Chem Lett., 16, 5036-5040, (2006).

[29] Caleta I, Grdisa M, Mrvos DS, Cetina M, Tralic KV, Pavelic K and Karminski G IL Farmaco, 59, 297-305, (2004).

[30] Geoffrey W, Tracey DB, Patrizia D, Angela S, Dong FS, Andrew DW and Malcolm FGS, Bioorg Med. chem. Lett., 10, 513-515, (2000).

[31] Terzioglu N., Gursoy A., Eur. J. Med. Chem. 38, 781-786, (2003).

[32] Singh V., Srivastava, V.K., Palit G., Shanker K., Arzneim-Forsch. Drug. Res., 42,993-996, (1992).

[33] Savini L., Chiasserini L., Travagli V., Pellerano C., Novellino E., Cosentino S., Pisano M.B., Eur. J. Med. Chem., 39, 113-122, (2004).

[34] Kalsi R., Shrimali M., Bhalla T.N., Barthwal J.P.; Indian J.Pharm. Sci., 41,353-359, (2006).

[35] Bernardino A., Gomes A., Charret K., Freitas A., Machado G., Cavalheiro M., Leon L., Amaral V., Eur. J.Med .Chem., 41, 80-87, (2006).

[36] Silva A.G., Zapata-Suto G., Kummerle A.E., Fraga C.A.M., Barreiro E .J., Sudo R.T., Bioorg Med. Chem., 13, 3431-3437, (2005).

Raj Narayan Sharma (1), K.P. Sharma (2) and S.N. Dixit (3)

(1) Department of Engg. Chemistry, NRI College of Engineering and Management &

(2,3) Chemical Research Laboratories, Govt. SMS Science College, (Jiwaji University), Gwalior, M.P.-474002 (India)

* E-mail: rajnarayan1974@gmail.com
Table I: Physical and analytical data of new compounds:
.Acid hydrazones derived from ethyl-2-[(N-benzoyl)
2,3-dichloroanilido] acetohydrazide.

[FORMULA EXPRESSION NOT REPRODUCIBLE IN ASCII]

S. Aldehyde/ [R.sub.1] [R.sub.2] MP
No. Ketone ([degrees]C)

1 Benzaldehyde H Ph 216

2. Vanilline H [FORMULA NOT 202
 REPRODUCIBLE
 IN ASCII]

3. 5-Chloro H [FORMULA NOT 217
 salicyladehyde REPRODUCIBLE
 IN ASCII]

4. 5-Bromo H [FORMULA NOT 213
 salicylaldehyde REPRODUCIBLE
 IN ASCII]

5. 2-Nitro H [FORMULA NOT 209
 vanilline REPRODUCIBLE
 IN ASCII]

6. O-Nitro H [FORMULA NOT 223
 benzaldehyde REPRODUCIBLE
 IN ASCII]

7. 2-Nitro H [FORMULA NOT 229
 5-Bromo REPRODUCIBLE
 vanillilne IN ASCII]

8. 3, 5 di chloro- H [FORMULA NOT 217
 2-hydroxy REPRODUCIBLE
 benzal dehyde IN ASCII]

9 3-Nitro-6- Me [FORMULA NOT 226
 hydroxy REPRODUCIBLE
 acetophenone IN ASCII]

10. Acetone Me Me 201

11. 2-Chloro H Ph - 228
 benzaldehyde Cl (2)

12. 4-N-N-Bis-2' H Ph - N - 237
 cyano ethyl [([CH.sub.2] -
 amino [CH.sub.2] -
 benzaldehyde [CH.sub.2])
 .sub.2]

13. 2-Methyl-4-N- H [FORMULA NOT 214
 N-bis 2' cyano REPRODUCIBLE
 ethyl amino IN ASCII]
 benzaldehyde

14. 2-Methoxy-4- H [FORMULA NOT 221
 N-N-bis 2' REPRODUCIBLE
 cyano ethyl IN ASCII]
 amino
 benzaldehyde

15 Acetophenone Me Ph 216

16. Salicylaldehyd H Ph - 228
 e OH (2)

17 Anisic H Ph - 234
 aldehyde [OCH.sub.3]
 (2)

18. [beta]- Me [FORMULA NOT 219
 Ionone REPRODUCIBLE
 IN ASCII]

S. Yield Formula Molecular Colour
No. (%) Weight formula

1 91 455 [C.sub.23][H.sub.18] White
 [O.sub.3][N.sub.3]
 [Cl.sub.2]

2. 84 501 [C.sub.24][H.sub.20] White
 [O.sub.5][N.sub.3]
 [Cl.sub.2]

3. 88 504.5 [C.sub.23][H.sub.16] White
 [O.sub.4][N.sub.3]
 [Cl.sub.3]

4. 92 597 [C.sub.23][H.sub.17] Silver
 [O.sub.4][N.sub.3] White
 [Cl.sub.2]Br

5. 75 546 Cream

6. 90 500 [C.sub.23][H.sub.17] White
 [O.sub.5][N.sub.4]
 [Cl.sub.2]

7. 58 672 [C.sub.24][H.sub.17] Cream
 [O.sub.5][N.sub.4]
 [Cl.sub.2]

8. 68 540 [C.sub.23][H.sub.19] White
 [O.sub.6][N.sub.4]
 [Cl.sub.2]

9 49 530 [C.sub.24][H.sub.19] Cream
 [O.sub.6][N.sub.4]
 [Cl.sub.2]

10. 44 407 [C.sub.19][H.sub.18] Cream
 [O.sub.3][N.sub.3]
 [Cl.sub.2]

11. 81 489.5 [C.sub.23][H.sub.17] White
 [O.sub.3][N.sub.3]
 [Cl.sub.3]

12. 64 576 [C.sub.29][H.sub.25] Light
 [O.sub.3][N.sub.6] brown
 [Cl.sub.2]

13. 86 590 [C.sub.30][H.sub.27] Brown
 [O.sub.3][N.sub.6]
 [Cl.sub.2]

14. 64 606 [C.sub.30][H.sub.27] Brown
 [O.sub.4][N.sub.6]
 [Cl.sub.2]

15 91 469 [C.sub.24][H.sub.20] White
 [O.sub.3][N.sub.3]
 [Cl.sub.2]

16. 57 471 [C.sub.23][H.sub.18] White
 [O.sub.4][N.sub.3]
 [Cl.sub.2]

1 7 71 485 [C.sub.24][H.sub.20] Yellow
 [O.sub.4][N.sub.3]
 [Cl.sub.2]

18. 38 551 [C.sub.30][H.sub.30] Buff
 [O.sub.3][N.sub.3]
 [Cl.sub.2]

S. Elemental analysis
No.

 Calcd. and Found

 C H O N Cl

1 54.85 3.71 9.14 12.00 20.28
 (5483) (3.70) (9.10) (11.99) (20.25)

2. 51.51 3.78 16.16 10.60 17.92
 (51.50) (3.75) (16.16) (10.50) (17.90)

3. 48.06 2.75 12.01 10.51 26.65
 (48.00) (2.72) (12.00) (10.50) (26.60)

4. 39.02 2.43 9.75 8.53 14.43
 (39.01) (2.42) (9.72) (8.51) (14.42)

5. 46.25 3.17 21.76 12.69 16.09
 (46.25) (3.15) (21.74) (12.67) (16.00)

6. 48.60 3.03 16.20 14.17 17.97
 (48.58) (3.01) (16.19) (14.15) (17.96)

7. 35.97 2.29 16.93 9.87 12.52
 (35.96) (2.29) (16.92) (9.86) (12.51)

8. 44.13 2.52 11.03 9.65 32.64
 (44.11) (2.51) (11.01) (9.64) (32.64)

9 48.00 3.29 18.82 13.17 16.70
 (48.00) (3.28) (18.81) (13.16) (16.69)

10. 47.68 4.30 10.59 13.90 23.50
 (47.66) (4.28) (10.58) (13.89) (23.49)

11. 49.93 3.12 8.32 10.92 27.69
 (49.92) (3.11) (8.31) (10.91) (27.68)

12. 56.05 4.24 6.79 17.83 15.07
 (56.04) (4.23) (6.78) (17.82) (15.06)

13. 56.90 4.53 6.59 17.31 14.63
 (56.89) (4.53) (6.58) (17.30) (14.61)

14. 55.08 4.39 9.58 16.76 14.17
 (55.07) (4.38) (9.57) (16.75) (14.16)

15 56.04 4.12 8.79 11.53 19.50
 (56.03) (4.11) (8.78) (11.52) (19.48)

16. 52.45 3.55 13.11 11.47 19.39
 (52.44) (3.54) (13.10) (11.46) (19.38)

1 7 53.68 3.94 12.63 11.05 18.68
 (53.67) (3.92) (12.61) (11.03) (18.67)

18. 61.88 5.60 7.17 9.41 15.91
 (61.87) (5.59) (7.14) (9.39) (15.89)

Table II: Tuberculostatic Activity of new acidhydrazones.

SI. No. Compounds

 1. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazide

 2. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of
 3-Nitro 6-hydroxy acetophenone

 3. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone of
 4-N,N-Bis 2' cyanoethylamino benzaldehyde

 4. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 2- methyl-4-N,N-Bis 2' cyanoethylamino benzaldehyde

 5. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 2-methoxy 4-N,N-Bis 2' cyanoethylamino benzaldehyde

 6. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of acetophenone

 7. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of salicylaldehyde

 8. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of anisicaldehyde

 9. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 2-Nitro vanilline

 10. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 2-chloro benzaldehyde

 11. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of benzaldehyde

 12. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 2-chloro benzaldehyde

 13. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of Vanilline

 14. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 5-Chloro Salicylaldehyde

 15. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 5-bromo Salicylaldehyde

 16. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of o-Nitro benzalaldehyde

 17. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 2-Nitro 5-bromo vanilline

 18. Ethyl-2-[(N-benzoyl)2,3-dichloroanilido] acetohydrazone
 of 3,5-dichloro-2-hydroxy benzaldehyde

SI. No. Growth at conc. [mg/mL] 10 100

 1. + 0

 2. + +

 3. + 0

 4. + +

 5. + +

 6. + 0

 7. + +

 8. + +

 9. + +

 10. + +

 11. + +

 12. + +

 13. + +

 14. + +

 15. + +

 16. + +

 17. + +

 18. + +

'+' and '0' indicate presence and inhibition of growth respectively.
COPYRIGHT 2010 Research India Publications
No portion of this article can be reproduced without the express written permission from the copyright holder.
Copyright 2010 Gale, Cengage Learning. All rights reserved.

Article Details
Printer friendly Cite/link Email Feedback
Author:Sharma, Raj Narayan; Sharma, K.P.; Dixit, S.N.
Publication:International Journal of Applied Chemistry
Date:Sep 1, 2010
Words:3798
Previous Article:Study of corrosion behavior of zirconium based multi constituent thin films.
Next Article:Inhibition of corrosion of mild steel in acid media by naturally occurring Citrullus colocynthis plant.
Topics:

Terms of use | Privacy policy | Copyright © 2019 Farlex, Inc. | Feedback | For webmasters