A facile green synthesis and in vitro antimicrobial activity 4H-pyrimido[2,1-b][1,3]benzothiazole derivatives using aluminum trichloride under solvent free conditions

Medicinal Chemistry Research

Volumn 21, Issue 11, 2012, Pages 3826-3834

  Sahu, Pramod K ^a   Sahu, Praveen K ^b   Lal, Jaggi ^a   Thavaselvam, D ^c   Agarwal, D D ^b  

^a JIWAJI UNIVERSITY   (India)

^b Jagdishprasad Jhabarmal Tibrewala University ^*  (India)

^c DEFENCE RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

4H pyrimido 2,1 b 1,3 benzothiazole derivatives; AlCl3; Antimicrobial activity; Green synthesis

Indexed keywords

ALDEHYDE; ALUMINUM DERIVATIVE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BENZOTHIAZOLE DERIVATIVE; CARBONYL DERIVATIVE; ETHYL 2 METHYL 4 (2 HYDROXY PHENYL) 4H PYRIMIDO[2,1 B] [1,3]BENZOTHIAZOLE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (2, 6 DICHLORO PHENYL) 4H PYRIMIDO [2,1 B][1,3]BENZOTHIAZOLE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (4 DIMETHYLAMINO PHENYL) 4H PYRIMIDO[2,1 B][1,3]BENZOTHIAZOLE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (4 HYDROXY 3 METHOXY PHENYL) 4H PYRIMIDO[2,1 B][1,3]BENZOTHIAZOLE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (4 HYDROXY PHENYL) 4H PYRIMIDO[2,1 B] [1,3]BENZOTHIAZOLE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (4 METHOXY PHENYL) 4H PYRIMIDO[2,1 B] [1,3]BENZOTHIAZOLE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (4 NITRO PHENYL) 4H PYRIMIDO[2,1 B] [1,3]BENZOTHIAZOLE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (PHENYL) 4H PYRIMIDO[2,1 B] [1,3]BENZOTHIAZOLE 3 CARBOXYLATE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FLAVUS; ASPERGILLUS FUMIGATUS; ASPERGILLUS NIGER; BACILLUS CEREUS; CATALYST; CONCENTRATION RESPONSE; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; NONHUMAN; ONE POT SYNTHESIS; POLYMERIZATION; PROVIDENCIA RETTGERI; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHI; STAPHYLOCOCCUS AUREUS;

EID: 84871443319     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9908-6     Document Type: Article

References (20)

1. Atwal KS, Swanson BN, Unger SE, Floyd DM, Moreland S, Hedberg A, O'reilly BC (1991) Dihydropyrimidine calcium channel blockers. 3. 3-carbamoyl-4-Aryl-1, 2, 3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid eaters as orally effective antihypertensive agents. J Med Chem 34(2):806-811
2. Bansal RK (2003) Heterocyclic chemistry, vol 3. New Age International Publishers, New Delhi, p 425
3. Chitra S, Devanathan D, Pandiarajan K (2010) Synthesis and in vitro microbiological evaluation of novel 4-Aryl-5-isopropoxycarbonyl-6-methyl-3,4- dihydropyrimidinones. Eur J Med Chem 45:367-371
4. Dallinger D, Kappe CO (2007) Microwave-Assisted synthesis in water as solvent. Chem Rev 107:2563-2591
5. Heilmann J, Wasescha MR, Schmidt TJ (2001) The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells. Bioorg Med Chem 9:2189-2194
6. Kappe CO (2000) Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc Chem Res 33:879-888
7. Kappe CO (2002) High-speed combinatorial synthetics utilizing microwave irradiation. Curr Opin Chem Biol 6:314-320
8. Khoshneviszadeh M, Edraki N, Javidnia K, Alborzi A, Pourabbas B, Mardaneh J, Miri R (2009) Synthesis and biological evaluation of some new 1,4-dihydropyrimidines containing different ester substitute and diethyl carbamoyl group as anti-tuberculosis agents. Bioorg Med Chem 17:1579-1586
9. Kralisch D, Stark A, Korsten S, Kreisel G, Onodruschka B (2005) Energetic, environmental and economic balances: spice up your ionic liquid research efficiency. Green Chem 7:301-309
10. Lanjewar KR, Rahatgaonkar AM, Chorghade MS, Saraf BD (2009) Synthesis and antimicrobial activity of 5-(2-Aminothiazol-4-yl)-3,4-dihydro-4- phenylpyrimidine-2(1H)-one. Ind J Chem 48B: 1732-1737
11. Matzke M, Stolte S, Thiele K, Juffernholz T, Arning J, Ranke J, Welzbiermann U, Jastorff B (2007) The influence of anion species on the toxicity of 1-Alkyl-3-methylimidazolium ionic liquids observed in an (eco) toxicological test battery. Green Chem 9:1198-1207
12. Miwatashi S, Arikawa Y, Matsumoto T, Uga K, Kanzaki N, Imai YN, Ohkawa S (2008) Synthesis and biological activities of 4-phenyl-5-pyridyl-1, 3-thiazole derivatives as selective adenosine A3 antagonists. Chem Pharm Bull (Tokyo) 56(8):1126-1137
13. Mosman T (1983) Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63
14. Pham T, Cho C, Yun Y (2010) Environmental fate and toxicity of ionic liquids: A review. Water Res 44:352-372
15. Ramon DJ, Yus M (2005) Asymmetric multicomponent reaction (AMCRs): The new frontier. Angew Chem Int Ed 44(11):1602-1634
16. Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S, Gougoutas JZ, O'Reillly BC, Schwartz J, Malley MF (1992) Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-Aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents. J Med Chem 35(17):3254-3263
17. Shaabani A, Rahmati A, Naderi S (2005) A novel one-pot threecomponent reaction: synthesis of triheterocyclic 4H-pyrimido[2, 1-b]benzazoles ring systems. Bioorg Med Chem Lett 15:5553-5557
18. Singh BK, Mishra M, Saxena N, Yadav GP, Maulik PR, Sahoo MK, Gaur RL, Murthy PK, Tripathi RP (2008) Synthesis of 2-sulfanyl-6-methyl-1,4- dihydropyrimidines as a new class of antifilarial agents. Eur J Med Chem 43:2717-2723
19. Vicini P, Garonikaki A, Incerti M, Busonera B, Poni G, Cabras CA, La Colla P (2003) Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases. Bioorg Med Chem 11:4785-4789
20. Zhu J, Bienayme HE (2005) Multicomponent reactions. Wiley-VCH, Wienheim