Design and synthesis: Novel quinazolin incorporated azetidinones and thiazolidinones as sedative, antibacterial and antifungal agents

S.S. Panda, P.V.R. Chowdary, S. Rani

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Several 3-chloro-1-[(2-phenylquinazolin-4-yl) oxy acetamidyl]-4- (substituted aryl)-2-azetidinones and 2-(substituted aryl)-3-[(2- phenylquinazolin-4-yl) oxy acetamidyl]-4-thiazolidinones were prepared by condensing 2-phenyl-4-(substituted benzylidine hydrazido methyloxy) quinazolines with chloroacetyl chloride and mercapto acetic acid respectively. These structures were established by IR and 1HNMR spectral data. These synthesized compounds were tested for their sedative, antibacterial and antifungal activities.
Original languageEnglish
Pages (from-to)84-89
Number of pages6
JournalIndian Drugs
Volume45
Issue number2
Publication statusPublished - 2008

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Quinazolines
Antifungal Agents
Hypnotics and Sedatives
Acetic Acid
Anti-Bacterial Agents
chloroacetyl chloride
2-azetidinone

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title = "Design and synthesis: Novel quinazolin incorporated azetidinones and thiazolidinones as sedative, antibacterial and antifungal agents",
abstract = "Several 3-chloro-1-[(2-phenylquinazolin-4-yl) oxy acetamidyl]-4- (substituted aryl)-2-azetidinones and 2-(substituted aryl)-3-[(2- phenylquinazolin-4-yl) oxy acetamidyl]-4-thiazolidinones were prepared by condensing 2-phenyl-4-(substituted benzylidine hydrazido methyloxy) quinazolines with chloroacetyl chloride and mercapto acetic acid respectively. These structures were established by IR and 1HNMR spectral data. These synthesized compounds were tested for their sedative, antibacterial and antifungal activities.",
author = "S.S. Panda and P.V.R. Chowdary and S. Rani",
note = "Cited By :2 Export Date: 10 November 2017 CODEN: INDRB Correspondence Address: Panda, S. S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal-576104, India; email: sivashankarpanda@yahoo.com Chemicals/CAS: quinazoline, 253-82-7 References: Sharma, S.D., Mehra, U., Pandhi, S.B., Khurana, J.P.S., Studies on fused -lactams: Synthesis and antibacterial activity of some pyridyl- and quinolyl-2-azetidinones (1988) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 27 B (5), pp. 494-497. , Dep. Chem., Panjab Univ., Chandigarh, India; Abbady, M.A., Awad, I.M.A., Kandeel, M.M., Synthesis and antimicrobial activity of 2-(arylideneamino)-4- phenyloxazoles, azetidinones, thiazolidinones, triazolines, and some spiroheterocycles (1988) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 27 B (1), pp. 90-92; Trivedi, P.B., Undavia, N.K., Dave, A.M., Bhatt, K.N., Desai, N.C., Synthesis and antimicrobial activity of 4-oxothiazolidines, 4-oxoazetidines, malonanilic acid hydrazines and pyrazoline derivatives of phenothiazine (1993) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 32 B (7), pp. 760-765; Hogale, M.B., Uthale, A.C., Nikam, B.P., Synthesis and antimicrobial activity of N10- arylidenehydrazidophenothiazine and their 4-thiazolidinones and 2-azetidinones (1991) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 30 B (7), pp. 717-720; Bhatt, J.J., Shah, B.R., Shah, H.P., Trivedi, P.B., Undavia, N.K., Desai, N.C., Synthesis of anti-HIV, anticancer and antitubercular 4-oxothiazolidines, 2-imino-4-oxo-thiazolidines and their 5-arylidine derivatives (1994) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 33 B (2), pp. 189-192; Lather, V., Chowdary, P.V.R., Synthesis and antimicrobial activity of N1(arylidine hydrazidomethyl)- indoles,2-(substituted aryl)-3-(N1-indolyl acetamidyl)-4-oxo-thiazolidines and 5-benzylidine derivatives of thiazolidinones (2003) Indian Journal of Pharmaceutical Sciences, 65 (6), pp. 576-579; Srivastava, V.K., Singh, S., Gulati, A., Shanker, K., Antiparkinsonian agents from quinazolinylthiazolidinones and azetidinones (1987) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 26 B (7), pp. 652-656; Mukerji, D.D., Nautiyal, S.R., Dhawan, B.N., Synthesis of some new acetamido and ureidomethyl-4(3H)-quinazolones as possible CNS depressant compounds (1979) Indian Journal of Pharmaceutical Sciences, 41 (1), pp. 33-36; Husain, M.I., Shukla, S., Synthesis and biological activities of 3-(2-aryl-4-oxothiazolidin-3-yl)- 2-phenylquinazolin-4(3H)-ones (1986) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 25 B (5), pp. 545-548; Giri, S., Nizamuddin, Singh, K.K., Synthesis and fungicidal activity of 1-aryl-2-aryloxymethyl-s-triazolo[5, 1-b]quinazol-5-ones (1982) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 21 B (4), pp. 377-378; Isaac, Y.A., Arsanious, M.H., Abd El-Nabi, H.A., Synthesis of new quinazoline derivatives of expected potential bioresponses (2002) Revue Roumaine de Chimie, 46 (12), pp. 1299-1307. , Volume Date 2001; Undavia, N.K., Trivedi, P.B., Shanishchara, A.P., Trivedi, V., Synthesis and antimicrobial evaluation of 1-[4-{4-(2-phenyl-4-oxo-3- quinazolinyl)phenyl}phenyl]-2-phenyl-4-arylidene-5-oxo-imidazoles (2004) Asian Journal of Chemistry, 16 (2), pp. 1214-1216; Vaid, R.K., Rao, B.V., Kaushik, B., Singh, S.P., Reaction of 2-aryl-3,1-benzoxazine-4-ones with hydrazine hydrate: A reinvestigation (1987) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 26 B (4), pp. 376-377; Issac, Y.A., Arsanious, M.H., Abd El-Nabi, H.A., A facile synthesis of 2-phenylquinazoline derivatives (2003) Egyptian Journal of Chemistry, 45 (5), pp. 929-946. , Volume Date 2002",
year = "2008",
language = "English",
volume = "45",
pages = "84--89",
journal = "Indian Drugs",
issn = "0019-462X",
publisher = "Indian Drug Manufacturers' Association",
number = "2",

}

Design and synthesis: Novel quinazolin incorporated azetidinones and thiazolidinones as sedative, antibacterial and antifungal agents. / Panda, S.S.; Chowdary, P.V.R.; Rani, S.

In: Indian Drugs, Vol. 45, No. 2, 2008, p. 84-89.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Design and synthesis: Novel quinazolin incorporated azetidinones and thiazolidinones as sedative, antibacterial and antifungal agents

AU - Panda, S.S.

AU - Chowdary, P.V.R.

AU - Rani, S.

N1 - Cited By :2 Export Date: 10 November 2017 CODEN: INDRB Correspondence Address: Panda, S. S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal-576104, India; email: sivashankarpanda@yahoo.com Chemicals/CAS: quinazoline, 253-82-7 References: Sharma, S.D., Mehra, U., Pandhi, S.B., Khurana, J.P.S., Studies on fused -lactams: Synthesis and antibacterial activity of some pyridyl- and quinolyl-2-azetidinones (1988) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 27 B (5), pp. 494-497. , Dep. Chem., Panjab Univ., Chandigarh, India; Abbady, M.A., Awad, I.M.A., Kandeel, M.M., Synthesis and antimicrobial activity of 2-(arylideneamino)-4- phenyloxazoles, azetidinones, thiazolidinones, triazolines, and some spiroheterocycles (1988) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 27 B (1), pp. 90-92; Trivedi, P.B., Undavia, N.K., Dave, A.M., Bhatt, K.N., Desai, N.C., Synthesis and antimicrobial activity of 4-oxothiazolidines, 4-oxoazetidines, malonanilic acid hydrazines and pyrazoline derivatives of phenothiazine (1993) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 32 B (7), pp. 760-765; Hogale, M.B., Uthale, A.C., Nikam, B.P., Synthesis and antimicrobial activity of N10- arylidenehydrazidophenothiazine and their 4-thiazolidinones and 2-azetidinones (1991) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 30 B (7), pp. 717-720; Bhatt, J.J., Shah, B.R., Shah, H.P., Trivedi, P.B., Undavia, N.K., Desai, N.C., Synthesis of anti-HIV, anticancer and antitubercular 4-oxothiazolidines, 2-imino-4-oxo-thiazolidines and their 5-arylidine derivatives (1994) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 33 B (2), pp. 189-192; Lather, V., Chowdary, P.V.R., Synthesis and antimicrobial activity of N1(arylidine hydrazidomethyl)- indoles,2-(substituted aryl)-3-(N1-indolyl acetamidyl)-4-oxo-thiazolidines and 5-benzylidine derivatives of thiazolidinones (2003) Indian Journal of Pharmaceutical Sciences, 65 (6), pp. 576-579; Srivastava, V.K., Singh, S., Gulati, A., Shanker, K., Antiparkinsonian agents from quinazolinylthiazolidinones and azetidinones (1987) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 26 B (7), pp. 652-656; Mukerji, D.D., Nautiyal, S.R., Dhawan, B.N., Synthesis of some new acetamido and ureidomethyl-4(3H)-quinazolones as possible CNS depressant compounds (1979) Indian Journal of Pharmaceutical Sciences, 41 (1), pp. 33-36; Husain, M.I., Shukla, S., Synthesis and biological activities of 3-(2-aryl-4-oxothiazolidin-3-yl)- 2-phenylquinazolin-4(3H)-ones (1986) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 25 B (5), pp. 545-548; Giri, S., Nizamuddin, Singh, K.K., Synthesis and fungicidal activity of 1-aryl-2-aryloxymethyl-s-triazolo[5, 1-b]quinazol-5-ones (1982) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 21 B (4), pp. 377-378; Isaac, Y.A., Arsanious, M.H., Abd El-Nabi, H.A., Synthesis of new quinazoline derivatives of expected potential bioresponses (2002) Revue Roumaine de Chimie, 46 (12), pp. 1299-1307. , Volume Date 2001; Undavia, N.K., Trivedi, P.B., Shanishchara, A.P., Trivedi, V., Synthesis and antimicrobial evaluation of 1-[4-{4-(2-phenyl-4-oxo-3- quinazolinyl)phenyl}phenyl]-2-phenyl-4-arylidene-5-oxo-imidazoles (2004) Asian Journal of Chemistry, 16 (2), pp. 1214-1216; Vaid, R.K., Rao, B.V., Kaushik, B., Singh, S.P., Reaction of 2-aryl-3,1-benzoxazine-4-ones with hydrazine hydrate: A reinvestigation (1987) Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 26 B (4), pp. 376-377; Issac, Y.A., Arsanious, M.H., Abd El-Nabi, H.A., A facile synthesis of 2-phenylquinazoline derivatives (2003) Egyptian Journal of Chemistry, 45 (5), pp. 929-946. , Volume Date 2002

PY - 2008

Y1 - 2008

N2 - Several 3-chloro-1-[(2-phenylquinazolin-4-yl) oxy acetamidyl]-4- (substituted aryl)-2-azetidinones and 2-(substituted aryl)-3-[(2- phenylquinazolin-4-yl) oxy acetamidyl]-4-thiazolidinones were prepared by condensing 2-phenyl-4-(substituted benzylidine hydrazido methyloxy) quinazolines with chloroacetyl chloride and mercapto acetic acid respectively. These structures were established by IR and 1HNMR spectral data. These synthesized compounds were tested for their sedative, antibacterial and antifungal activities.

AB - Several 3-chloro-1-[(2-phenylquinazolin-4-yl) oxy acetamidyl]-4- (substituted aryl)-2-azetidinones and 2-(substituted aryl)-3-[(2- phenylquinazolin-4-yl) oxy acetamidyl]-4-thiazolidinones were prepared by condensing 2-phenyl-4-(substituted benzylidine hydrazido methyloxy) quinazolines with chloroacetyl chloride and mercapto acetic acid respectively. These structures were established by IR and 1HNMR spectral data. These synthesized compounds were tested for their sedative, antibacterial and antifungal activities.

M3 - Article

VL - 45

SP - 84

EP - 89

JO - Indian Drugs

JF - Indian Drugs

SN - 0019-462X

IS - 2

ER -