Volume : IV, Issue : III, March - 2014
MOSQUITO–LARVICIDAL, ANTI–BACTERIAL AND ANTI–FUNGAL PROPERTIES OF NOVEL 2, 4–DISUBSTITUTED–[1, 3] – THIAZOLES
Mr Prakash Anil Castelino, Dr Jagadeesh Prasad Dasappa, Dr Prashantha Naik, Mr Sharath Chandra K. , Ms Anusha Kumari G. Y.
Abstract :
A series of novel hydrazones of 2, 4–disubstituted–[1, 3] – thiazole (5) were prepared by the reaction of thiosemicabazone (3) with different substituted phenacyl halides (4) in the presence of dimethylformamide as a solvent. The requisite thiosemicarbazone (3) was synthesized by the treatment of thiosemicabazide (1) with 2, 4–dichloro–5–fluroacetophenone (2) in presence of catalytic amount of mineral acid.  All the novel compounds were confirmed and characterized by elemental analysis, FT–IR, 1H–NMR,      13C–NMR and Mass spectra and were subjected to anti–bacterial, anti–fungal activity studies and also screened for mosquito–larvicidal activitiy studies against two pathogenic vectors namely; Anopheles stephenesis (malaria vector) and C. tritaeniorhynchus (Japanese encephalitis). Among the novel 2, 4–disubstituted [1, 3]– thiazoles (5a– 5o), the compounds 2–{2–[1–(2, 4–dichloro–5–fluorophenyl) ethylidene] hydrazinyl}–4–(4–fluorophenyl)–[1, 3]–thiazole (5j)  and 2–{2–[1–(2, 4–dichloro–5–fluorophenyl) ethylidene] hydrazinyl}–4–(4–nitrophenyl) –[1, 3] –thiazole (5m) exhibit anti–bacterial and anti–fungal properties. Though the mosquito–larvicidal activity is low among the novel derivatives, yet,  4–(4–omophenyl)–2–{2–[1–(2, 4–dichloro–5–fluorophenyl) ethylidene] hydrazinyl} –[1, 3]–thiazole (5i)  and 2–{2–[1–(2, 4–dichloro–5–fluorophenyl) ethylidene] hydrazinyl}–4–(4–fluorophenyl)–[1, 3]– thiazole (5j) may be recommended as  mosquito larvicidal agents for further studies
Keywords :
Mosquito–larvicidal activity Anti–bacterial activity Anti–fungal activity Hydrazones of 1 3–thiazole Schiff base.
Article:
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DOI : 10.36106/ijar
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Prakash Anil Castelino, Jagadeesh Prasad Dasappa, Prashantha Naik, Sharath Chandra K., Anusha Kumari G. Y., MOSQUITO-LARVICIDAL, ANTI-BACTERIAL AND ANTI-FUNGAL PROPERTIES OF NOVEL 2, 4-DISUBSTITUTED-[1, 3]‾THIAZOLES Indian Journal of Applied Research, Vol.IV, Issue. III
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References :
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Prakash Anil Castelino, Jagadeesh Prasad Dasappa, Prashantha Naik, Sharath Chandra K., Anusha Kumari G. Y., MOSQUITO-LARVICIDAL, ANTI-BACTERIAL AND ANTI-FUNGAL PROPERTIES OF NOVEL 2, 4-DISUBSTITUTED-[1, 3]‾THIAZOLES Indian Journal of Applied Research, Vol.IV, Issue. III
Almasirad A, Tajik M, Bakhtiari D, Shafiee A, Abdollahi M, Jafar Zamani M, Khorasani R and Esmaily HJ. (2005) J Pharm Pharm Sci 8(3) 419. Argyropoulou I, Geronikaki A, Vicini P and Zanib F. (2009). Arkivoc VI: 89. Bauer AW, Kirby WMM, Sherris JC and Turck M. (1966) Am J Clin Pathol 45: 493. Bell FW, Cantrell AS, Hoegberg M, Jaskunas SR, Johansson NG, Jordan CL, Kinnick MD, Lind P and Morin JM. (1995) J Med Chem 38: 4929. Bhattacharya P, Leonard JT and Roy K. (2005) Bioorg Med Chem 13: 1159. Bijev A. (2006) Lett Drug Des Discov 3: 506. Bruice PY. (2006) Organic Chemistry: Pearson Publications: Indian Ed. 751 Chandrasekhar S, Narsimulu CH, Sultana SS and Reddy NRK. (2002) Org Lett 4: 4399. Cocco MT, Congiu C, Lilliu V and Onnis V. (2005) Bioorg Med Chem 14: 366. Dadson RM and King LC. (1945) J Am Chem Soc 67: 2242. Dimmock JR, Vasishtha SC and Stables JP. (2000) Eur J Med Chem 35: 241. Furniss BS, Hannaford AJ, Smith PWG and Tatchell AR. (2007) Vogel’s Textbook of Practical Organic Chemistry. Dorling Lindersley Ltd : Indian Edition, III Ed. 782 Geronikaki A, Hadjipavlou–Litina D, Zablotskaya A and Segal I. (2007) Bioinorg Chem Appl 2007:92145. Gindher T. Reddy RB, Prasanna B and Chandra Mouli GVP. (2001) Ind J Chem 40B: 1279. Gu XH, Wan XZ and Jiang B. (1999) Bioorg Med Chem Lett 9: 569. Hantzsch and Weber HJ. (1987) Ber Chem Res 20: 3118. Haviv F, Ratajczyk JD, DeNet RW, Kerdesky FA, Walters RL, Schmidt SP, Holms JH, Young PR and Carter GW. (1988) J Med Chem 31: 1719. Heldebrant D and Jessop PG. (2003) J Am Chem Soc 125: 5600. Jiang B and Gu XH. (2000) Bioorg Med Chem 8: 363. King LC and Halavacck RJ. (1950) J Am Chem Soc 72: 3722 Kumar Y, Green R, Borysko KZ, Wise DS, Wotring LL and Townsend LB. (1993) J Med Chem 36: 3843. Lednicer D, Mitscher LA and George GI. (1990) Organic Chemistry of Drug Synthesis. Wiley: New York. Vol. 4: 95. Bruice PY. (2006) Organic Chemistry: Pearson Publications: Indian Ed. 751 Lima PC, Lima LM, Silva KC, Leda PH, Miranda ALP, Fraga CAM and Barreiro EJ. (2000) Eur J Med Chem 35: 187. Mean RGJ and Mocelo CRO. (1994) Chem Abstr 20: 244806. Metzger JV. (1984) Comprehensive Heterocyclic Chemistry. Pergamon: NewYork. I, Vol. 6: 328. Murineddu G, Loriga G, Gavini E, Peana AT, Mule AC and Pinna GA. (2001) Arch Pharm 334: (12) 393. Patt WC, Hamilton HW, Taylor MD, Ryan MJ, Taylor DG, Connolly CJ, Doherty AM, Klutchko SR and Sircar I. (1992) J Med Chem 35: 2562. Radhwan MAA, Ragab EA, Sabry NM and El–Shenawy SM. (2007) Bioorg Med Chem 15: 3832. Rashed N, El Massry AM, El Ashry ESH, Amer A and Zimmer H. (1990) J Heterocycl Chem 27: 691. Raymond M, Prato G and Ratsira D. (1993) PROBIT Analysis of Mortality Assays Displaying Quantal Response. Rollas S and Kucukguzel SG. (2007) Molecule 12: 1910. Salgin–Goksen U, Gokham–Keleci N, Gostal O, Koysal Y, Kilici E, Isik S, Aktay G and Ozalp M. Bioorg Med Chem 12: 3149. Sharma RN, Xavier FP, Vasu KK, Chaturvedi SC and Pancholi SS. (2009) Journal of Enzyme Inhibition and Medicinal Chemistry 24: 890. Silva GA, Costa LMM, Brito FCF, Miranda ALP, Barreiro EJ and Fraga CAM. (2004) Bioorg Med Chem 12: 3149 Surray AR. (1949) J Am Chem Soc 71: 3354. Trautman HD and Longe LM. (1948) J Am Chem Soc 70: 3436. Todeschini AR, De Miranda ALP, Da Silva KCP, Parrini SC and Barreiro EJ. (1988) Eur J Med Chem 33: 189. Tsuji K and Ishikawa H. (1994) Bioorg Med Chem Lett 4: 1601. Vardar–Unlu G, Candan F, Sokmen A, Daferera D, Polissiou M, Sokmen E. Domez M and Tepe B. (2003) J Agric Food Chem 51(1): 63. Venugopala KN, Krishnappa M, Nayak SK, Subrahmanya BK, Vaderapura JP, Chalannavar RK, Gleiser RM and Odhav B. (2013) Eur J Med Chem 65: 295. Walcourt A, Loyevsky M, Lovejoy DB, Gordeuk VR and Richardson DR. (2004) Int J Biochem Cell Biol 36: 401. Wilson KJ, Illig CR, Subasinghe N, Hoffman JB, Rudolph MJ, Soll R, Molloy CJ, Bone R, Green D, Randall T, Zhang M, Lewandowski FA, Zhou Z, Sharp C, Maguire D, Grasberger B, Desjarlais RL and Spurlino J. (2001) Bioorg Med Chem Lett 11: 915. World Health Organization. (1981) WHO/ VBC/ 81: 807.
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