The chemistry and biological potential of azetidin-2-ones

Arya, Nikhilesh; Jagdale, Archana Y.; Patil, Tushar A.; Yeramwar, Shradha S.; Holikatti, Sidharam S.; Dwivedi, Jaya; Shishoo, C. J.; Jain, Kishor S.

doi:10.1016/j.ejmech.2014.01.002

Cited by 91 publications

(50 citation statements)

References 162 publications

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“…(Arya et al, 2014;Singh & Sudheesh, 2014;Zeng et al, 2014;Zarei et al, 2013). In addition to their well recognized antibiotic activity, β-lactams exhibit various other biological activities such as thrombin, human, HIV-1 protease, human leukocyte elastase, cholesterol absorption inhibition and antifungal, anticancer, antidiabetic and potential antimalarial properties (Mehta et al, 2010;Singh et al, 2011;Ebrahimi & Jarrahpour, 2014).…”

Section: Methodsmentioning

confidence: 99%

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1-(Morpholin-4-yl)-4-(2-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one

et al. 2014

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Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.002 Å; R factor = 0.045; wR factor = 0.098; data-to-parameter ratio = 17.5.In the title compound, C 22 H 21 N 3 O 5 , the -lactam (azetidin-2-one) ring is nearly planar [maximum deviation = 0.010 (1) Å ] and makes dihedral angles of 69.22 (5), 55.32 (5) and 89.42 (4) with the least-squares planes formed by the four C atoms of the morpholine ring, which adopts a chair conformation, the benzene ring and the xanthene ring system, respectively. In the crystal, C-HÁ Á ÁO hydrogen-bond contacts connect neighbouring molecules into infinite zigzag chains running parallel to the b axis. Related literature ExperimentalCrystal data

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Section: Methodsmentioning

confidence: 99%

“…For general background to -lactams, see: Arya et al (2014); Ebrahimi & Jarrahpour (2014); Singh & Sudheesh (2014); Zeng et al (2014); Zarei et al (2013); Jarrahpour & Ebrahimi (2010); Mehta et al (2010); Singh et al (2011). For geometric analysis, see : Cremer & Pople (1975); Nardelli (1995).…”

Section: Related Literaturementioning

confidence: 99%

1-(Morpholin-4-yl)-4-(2-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one

et al. 2014

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“…1 This key role has led to numerous routes to the b-lactam core. 2 One particularly effective route involves the addition of ketenes to imines.…”

Section: Introductionmentioning

confidence: 99%

Use of the thiophenesulfonyl protecting group in the catalytic, asymmetric synthesis of unprotected β-lactams

Wang

Calter

2015

Tetrahedron Letters

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“…The b-lactam heterocycles are considered as an important contribution of science to humanity, since they have been constituents of living organisms, natural products, drugs, and many more substances useful to mankind and society in all walks of life (Brown, 1989;Isaacs, 1976;Singh, 2003). Azetidin-2-ones, commonly referred as b-lactams, represent a unique ring system, with interesting chemistry and great biological potential (Arya et al, 2014). Besides its wellknown antibiotic activity, this ring system exhibits a wide range of activities, attracting the attention of researchers (Chimento et al, 2013;Jaishree et al, 2012;Bhati and Kumar, 2008;Halve et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Study of new β-lactams-substituted s-triazine derivatives as potential bioactive agents

2014

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In our continuous effort toward synthesis of potential bioactive agents, two series of benzonitriles/ nicotinonitriles endowed with b-lactams bound to s-triazine skeleton were synthesized by applying an efficient palladium catalyzed C-C Suzuki coupling reaction. The synthesized compounds were screened for their in vitro antimicrobial against different human pathogenic microorganisms and prostate cancer PC3 cells. Some compounds displayed remarkable antimicrobial activity and noticeable anticancer activity. It was observed that both benzonitrile and nicotinonitrile sets are essential to increase the different pharmacological activities. The new synthesized compounds were characterized by FT-IR, 1 H NMR, 13 C NMR, and MS analysis.

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The chemistry and biological potential of azetidin-2-ones

Cited by 91 publications

References 162 publications

1-(Morpholin-4-yl)-4-(2-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one

1-(Morpholin-4-yl)-4-(2-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one

Use of the thiophenesulfonyl protecting group in the catalytic, asymmetric synthesis of unprotected β-lactams

Study of new β-lactams-substituted s-triazine derivatives as potential bioactive agents

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