Synthesis and in vitro study of methylene-bis-tetrahydro[1,3]thiazolo[4,5- c]isoxazoles as potential nematicidal agents

• Published in: European journal of medicinal chemistry Vol. 45; no. 6; pp. 2353 - 2358
• Main Authors: Srinivas, Avula, Nagaraj, Adki, Reddy, Cherkupally Sanjeeva
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.06.2010; Elsevier
• Subjects: Animals; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal activity; Antifungal agents; Antinematodal Agents - chemical synthesis; Antinematodal Agents - chemistry; Antinematodal Agents - pharmacology; Biological and medical sciences; Caenorhabditis elegans - drug effects; Chalcone - chemistry; Chemical control; Chemistry, Medicinal; Control; Fundamental and applied biological sciences. Psychology; Fungi - drug effects; Isoxazoles - chemical synthesis; Isoxazoles - chemistry; Isoxazoles - pharmacology; Lethal Dose 50; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Medical sciences; Methylene-bis-tetrahydro[1,3]thiazolo[4,5- c]isoxazoles; Microbial Sensitivity Tests; Nematicidal activity; Nematoda - drug effects; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Phytopathology. Animal pests. Plant and forest protection; Protozoa. Invertebrates; Science & Technology; Thiazolidines - chemistry; Tylenchoidea - drug effects; Antifungal activity; Methylene-bis-tetrahydro[1,3]thiazolo[4,5- c]isoxazoles; Nematicidal activity; Methylene-bis-tetrahydro[1,3]thiazolo[4,5-c]isoxazoles; CP-060S; SOLID-PHASE SYNTHESIS; EFFICIENT; Nematicide; Trichophyton; Pesticides; Ditylenchus; In vitro; Biological activity; Diphenylmethane derivatives; Fungi; Caenorhabditis elegans; Antifungal agent; Chlorine Organic compounds; Helmintha; 14,5-clisoxazoles; Nemathelminthia; Methylene-bis-tetrahydro[1,3]thiazolo; Fungi Imperfecti; Fluorine Organic compounds; Invertebrata; Aspergillus fumigatus; Chemical synthesis; Nematoda
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2010.02.014

A series of methylene-bis-tetrahydro[1,3]thiazolo[4,5- c]isoxazoles 6 were synthesized by the reaction of chalcone derivative of methylene-bis-thiazolidinone 5 with hydroxylamine hydrochloride. The chemical structures of newly synthesized compounds were elucidated by IR, 1H, 13C NMR, MS and elemental analyses. The compounds 6a– g were evaluated for their nematicidal activity against Ditylenchus myceliophagus and Caenorhabditis elegans, compound 6e and 6f showed appreciable nematicidal activity. Further the compounds 6a– g were screened for their antifungal activity against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185) and Trichophyton mentagrophytes (IFO 40996). The compounds 6b and 6f displayed notable antifungal activity against all the microorganisms employed. The activity of these two compounds is almost equal to the standard. It is also interesting to note that the compounds 6b, 6f and 6g showed activity towards C. albicans at the concentration of 3.75 μM, which is less than the concentration of the standard Amphotericin B. A series of methylene-bis-tetrahydro[1,3]thiazolo[4,5- c]isoxazoles have been synthesized and screened for their in vitro antifungal and nematicidal activities. [Display omitted]