Several new 2-hydroxy-1-naphthal-2'-[5' (p-substituted/unsubstituted) pheny- 1',3',4' oxadiazole/thiadiazole] (IIa-j) have been reported by the condensation of 2-hydroxy-1-naphthaldehyd with 2-amino-4(substituted/unsubstituted) pheny1 thiadiazole/ oxadiazole in benzene. The synthesized compounds were characterized by Ir and nmr spectra. All these synthesized compounds have been screened against Aspergillus niger for antifungal activity

Santosh Pathak1 and S.C. Mehra1, Dhananjaya Singh1,2*,

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Recent Research in Science and Technology 2010, 2(9): 48-50 ISSN: 2076-5061 www.recent-science.com  CHEMISTRY Synthesis of some New 2-Hydroxy-1-naphthal-2'-[5'-Pheny-1',3',4'-oxadiazole/thiadiazole] as Potential Antifungal Agents  Dhananjaya Singh1,2∗, Santosh Pathak1 and S.C. Mehra1 1Department of Chemistry, Bareilly College, Bareilly (U.P) India-243006 2Department of Chemistry, PPN College Kanpur    Abstract Several new 2-hydroxy-1-naphthal-2'-[5' (p-substituted/unsubstituted) pheny- 1',3',4' oxadiazole/thiadiazole] (IIa-j) have been reported by the condensation of 2-hydroxy-1-naphthaldehyd with 2-amino-4(substituted/unsubstituted) pheny1 thiadiazole/ oxadiazole in benzene. The synthesized compounds were characterized by Ir and nmr spectra. All these synthesized compounds have been screened against Aspergillus niger for antifungal activity.                                                          ∗ Corresponding Author, Email: dhananjay360@gmail.com Introduction Imines have been reported to possess biological activity1-2. Various 1,3,4 thaidiazole/oxadiazole compounds have also been reported to have significant biological activities, specially fungicidal3-15 and bactericidal16-20. The fact were also considered during heterocyclic derivatives preparation that presence of hydroxyl, methoxy, ethoxy etc. (electron donating   groups) in the phenyl nucleus increases the activity of the parent compound21.      In the present study attempts were made to synthesise some new 2-hydroxy-1-naphthal-2']5'-(substituded/unsubstitued) phenyl-1',3',4'Thaidiazole / oxadiazole] derivatives and their antifungal-activity.         Experimental Melting points were determined in open capillary tubes and are uncorrected. Purity of compounds were checked by TLC using silica gel-G. Ir spectra were recorded on a Perkin-Elmer spectrophotometer and nmr spectra (CDC13) were recorded on Varian EM 360L spectrometer using T.M.S. as an internal standard.   Synthesis of 2-Hydroxy-1-naphthal-2'-[5-'phenyl-1',3',4',-thiadiazole]      A mixture of 2-hydroxy-1-naphthaldehyde (0.01mole) in dry benzene (50ml) and 2-amino-5phenyl-1,3,4 thiadiazole (0.01mole) was refluxed on water bath for 10 hours. The solution was then allowed to cool and the separated solid was recrystallized fram methanol. (Yield-62%) MP-178-1790C.  Ir (KBr)-1260cm-1 (C-N), 685cm-1 (C-S-C), 1620 cm-1, 1610cm-1, 1580cm-1 (C=N). pmr δ=7.6 (5H,m, Ar-H), δ=8.1 (H,s,-CH=N-), δ=7.8-8.6 (6H,m, Naphthyl proton) δ=9.2 (H,s,-OH). The compounds thus obtained are listed in table – 1. Dhananjaya Singh et al./Rec Res Sci Tech 2 (2010) 48-50   Table – 1: Physical and analytical data of Compounds Comp. No. X R Molecular Formula Yield (%) M.P(0C) IIa 2-Amino-5phenyl (subs/unsubs.) Thaidiazole -H C19H13N3SO 62 178-179 IIb ” -p-OH   C19H13N3O2S 56 183-184 IIc ” -P-Cl  C19H12N3OSCl 60 163-164 IId ” -p-OCH3 C20H15N3O2S 68 192 IIe ” -p-NO2 C19H12N4O3S 54 158 IIf 2-Amino-5phenyl (subs/unsubs.)oxadiazole H C19H13N3O2 62 95 IIg ” -p-OH C19H13N3O3 52 85-86 IIh ” -p-Cl C19H12N3O2CI 55 88-89 Iii ” -p-OCH3 C20H15N3O3 58 100-101 IIj ” -p-NO2 C19H12N4O4 55 80-82 satisfactory NS analyses were obtained for all compounds   Table – 2: Antifungal activity data for newly synthesized compounds against  Aspergillus  niger at optimum temp. 28 ± 10 C after 10 days incubation) Comp. No Dose in % Average colony Diam.(in mm)in PDA medium 22-23 % of inhibition Control - 60.66 - IIa .20 14.22 76.55 IIb .20 13.11 78.38 IIc .20 10.11 83.33 IId .20 4.44 92.68 IIe .20 27.33 54.94 IIf .20 16.66 72.53 IIg .20 11.11 81.68 IIh .20 10.33 82.29 Iii .20 4.92 91.88 IIj .20 30.36 49.95 Carbendazine(Std.drug) 0.15 .20 100.00   Fungicidal Screening All synthesized compounds were screened for their antifungal activity against aspergillus niger by using food and poison technique. The compounds were tested at 0.2% concentration. Fungus cultures were incubated at 28 ± 10 c for 10 days. The efficiency of all antifungal compound was recorded by measuring the radial growth of the fungal colony in mm. Under similar condition control experiment was carried out by using carbendazine as a standard for comparison. % Inhibition by various compounds were calculated from the formula % inhibition = (C-T)x100/C, where C = dia. of zone inhibition in control plates and T = dia. of zone of inhibition in treated plate. All data are given in table (2).  Result and Discussion The fungal screening data indicates that all synthesized compounds tasted were found statistically superior over control but inferior to that of standard antifungal (Carbedazin) compound. Two compound (IId, IIi) showed a marked inhibition of the fungal growth on vitro tests. Compound IIa, IIb, IIc, IIg and IIh also showed a significant level of inhibition, were found to inferior than the compound IId and IIi and the standard which has shown complete inhibition of the fungal colony. It can also be concluded from the result that compound with –Cl and –OCH3   group possess more activity as most of the compounds possessing these groups showed significant level of antifungal activity.  Acknowledgement The authors are thankful to Dr. S.K. Tondon (Sr. Scientist), division of Pharmacology, IVRI, Izzatnagar, Bareilly for helping him carrying out pharmacological screening of compounds and Dr. P.K. Kaicher, Deputy Director, Shri Ram Institute, Delhi for interpretation of Ir and pmr Spectra.   Reference 1. D.N. Dhar and C.L. Taploo, J. Sci. Ind. Res; 1982, 40: 501. 2. M.R. Manrao, R.K. Sethi, R.C. Sharma and P.S. Kalsi, J. Indian chem. Soc; 1996, 73: 695. 3. S.A. Khanum, S. Shashikant, S.G. Satyanarayan, S. Lokesh and S.A. Deepak, Gaertn Pest Dhananjaya Singh et al./Rec Res Sci Tech 2 (2010) 48-50  Management science; 2009, 65: 776-780 doi, 10, 1002/Ps, 1752.  4. C. Lukaszuk, E. Krajewska – Kulak, A. Niewiadony, J. Stachowicz, U. Glaszcz, E. Oksiejczuk; Advance in medical science; 2007, 52: 26-29.  5. W. Rzeski, J. Matysiak, M. Kandefer – Szerszen; Bioorg Med Chem; 2007, 15; 3201 – 7. 6. S.N. Swamy, Basappa, BS Priya, B. Prabhuswamy, BH Doreswamy, J. S. Prasad, K.S. Rangappa; Eur J. Med. Chem; 2006, 41: 531-8. 7. F. Foroumadi, M. Daneshtalab, A. Shafiee; Arznein- Forsch./Durg Res. 1999, 49: 1035.  8. Y.J. Ram and H.N. Pandey, Agric. Bio. Chem; 1993, 37: 2191.  9. Y. Yasuda and Y Uciyama, Japan Kokai; 1974, 7.020: 335 Chem. Abstr. 1974, 81: 73399. 10. J.C. Debourage, D. Pillon and S. Trinh, Ger. Often; 1974, 3:, 361, 613, Chem. Abstr; 1974, 81: 91537.  11. Balakrishna Kulluraya et al, Ind. Jr. Het. Chem. 1996, 5:  273-276.  12. R.S. Sharma and S.C. Bahel, J. Ind. Soc; 1982, LIX: 887-800. 13. Nizamuddin, Madhulika Mishra, Manoj Kumar Srivastava and Mukhtar Hussain Khan, In. Jr. of Chem; 2001, 40B: 49-53. 14. Vandana Diwivedi and R.K. Agarwal, Asian Jr. Chem; 1992, 4: 780-784.  15. G. Palazzo and B. Silvestrini, U.S. Pat, 1970, 3: 502608 Chem Abstr. 1970, 72 132741. 16. W.R. Sharma, J. Org. Chem. 1961, 26: 88. 17. Jagmohan, Ind. J. hetero Chem. 1999, 9, 143-146. 18. A.M. Dhiman and K.N. Wadodkar, Ind. Jr. Chem; 2001, 40B:  636-639. 19. Rajini Gupta, A.K. Gupta, Satya Paul and P. Somal, Ind. J. Chem; 2000, 39B: 847-852. 20. M.R. Manroa and S. Kohli;  J. Indian Chem. Sco. 1986, 63: 348. 21. M. Rai, B-Kaur and B.S. Dhir, J. Ind. Chem. Soc; 1982, 59: 416, M.R. Manrao and B.S. Dhir, Pesticides 1980, p-30. 22. C.J. Alexopoulos and C.W. Mims, Intro. Mycology 3rd Ed. Wiley Eastern Ltd. (1993). 23. R.C. Mehrotra and K.R. Aneja, An. Intro. to Mycology, Wiley Eastern Ltd (1990). 

Synthesis of some New 2-Hydroxy-1-naphthal-2'-[5'-Pheny-1',3',4'-oxadiazole/thiadiazole] as Potential Antifungal Agents

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Synthesis of some New 2-Hydroxy-1-naphthal-2'-[5'-Pheny-1',3',4'-oxadiazole/thiadiazole] as Potential Antifungal Agents

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