Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one

Pandeya, S. N.; Sriram, Dharmarajan; Nath, Gopal; Clercq, Erik De

doi:10.1016/s0031-6865(99)00010-2

Cited by 241 publications

(167 citation statements)

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“…Some of them have exhibited promising pharmacological activities, such as anticonvulsant, antihypertensive, antidiabetic, antibacterial, antitumor, antihistaminic, and antiinflammatory activities [2][3][4][5][6]. Hence these heterocycles have become an attractive target for combinatorial chemistry groups involved in drug discovery and crop protection.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-(3-aminopropyl)-2-(p-tolylamino)quinazolin-4(3H)-one, C18H20N4O

Wang

Xiao

Yang

2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo a solution of ethyl 2-((triphenylphosphoranylidene)amino)-benzoate iminophosphorane (1.27 g, 3 mmol) in THF (10 mL), 1-isocyanato-4-methylbenzene (0.41 g, 3 mmol ) was added under nitrogen atmosphere at 0-5°C. After the reaction mixture stood for 12 h in 0-5°C to give ethyl 2-(((p-tolylimino)methylene)-amino)benzoate, which was directly used without further purification, whereafter the above resulting solution was added dropwise to propane-1,3-diamine (0.33 g, 4.5 mmol) in THF 5 mL and stirred for 24 h at room temperature. The mixture was concentrated under vacuum until a slightly viscous solution was generated, followed by precipitation in CH 3 OH to give the title compound in 65% yield. Crystals suitable for single-crystal Xray diffraction were obtained by recrystallization from a mixed solvent of methanol and dichloromethane (1:2 = v/v) at room temperature. 1 H NMR (DMSO-d 6 , 500 MHz) d: 7.95 (d, -NH-, J = 7.8 MHz, 1H), 7.60 -7.49 (m, Ar-H, 3H), 7.24-7.13 (m, Ar-H, 5H), 5.43 (s, NH 2 , 2H), 4.17 (t, Quinazolinone-CH 2 -, J 1 = 5.00 Hz, J 2 = 5.95 Hz, 2H), 2.63 (t, -CH 2 -NH 2 , J 1 = 5.95Hz, J 2 = 5.50 Hz, 2H), 2.29 (s, CH 3 , 3H), 1.92 (m, -C-CH 2 -C-, 2H).13 C NMR (DMSO-d 6 , 125 MHz) d: 162.8, 134.6, 132.1, 129.4, 126.7, 123.0, 122.3, 117.7, 37.0, 29.7, 21.0. Experimental detailsThe structure was solved by direct methods with the SHELXS-97 program [1] yielding four crystallographic independant molecules in the asymmetric unit. All H-atoms were positioned with idealized geometry and refined isotropic (U iso (H) = 1.5U eq (C) for methyl H atoms and U iso (H) = 1.2U eq (C) for all other H atoms) using a riding model with C-H = 0.93 Å, 0.97 Å and = 0.96 Å, N-H = 0.86 Å.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-(3-aminopropyl)-2-(p-tolylamino)quinazolin-4(3H)-one, C18H20N4O

Wang

Xiao

Yang

2013

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The antifungal activity was carried out by agar diffusion method 23 against the fungi AN, CA, and CNE.…”

Section: Antifungal Activitymentioning

confidence: 99%

Untitled

2015

Hygeia.J.D.Med.

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“…Schiff bases are an important class of compounds in medicine and pharmaceutics. They show biological applications including antibacterial [1][2][3][4][5][6], antifungal [3][4][5][6], antitumor [7,8], antioxidant [9,10], anti-inflammatory [11], antihypertensive [12], anti-HIV [13], antifilarial [14], anticonvulsant [15], herbicidal, insecticidal, schistosomicidal and anthelmintic activities [16]. Schiff bases are used as protective agents in natural rubber [17].…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis and evaluation of antibacterial activity of 2,2'-(naph- thalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) derivatives

Venkatesan¹,

Satyanarayana²,

Sivakumar³

2012

Bull. Chem. Soc. Eth.

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ABSTRACT. A series of Schiff base of 2,2'-(naphthalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) (4a-m) derivatives has been synthesized by the acid catalyzed condensation of aryl/hetero aromatic aldehydes with 2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide (3) under microwave irradiation and conventional method for comparison. The structures of all the newly synthesized compounds have been characterized by IR, 1 H NMR, 13 C NMR and Mass spectra. All the synthesized compounds have been screened for their in vitro antibacterial activity.

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Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one

Cited by 241 publications

References 2 publications

Crystal structure of 3-(3-aminopropyl)-2-(p-tolylamino)quinazolin-4(3H)-one, C18H20N4O

Crystal structure of 3-(3-aminopropyl)-2-(p-tolylamino)quinazolin-4(3H)-one, C18H20N4O

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Microwave-assisted synthesis and evaluation of antibacterial activity of 2,2'-(naph- thalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) derivatives

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