Synthesis of some new 4-aryloxmethylcoumarins and examination of their antibacterial and antifungal activities

Basanagouda, Mahantesha; Kulkarni, Manohar V.; Sharma, Deepak; Gupta, Vivek K.; Pranesha,; Sandhyarani, P.; Rasal, Vijaykumar P.

doi:10.1007/s12039-009-0058-z

Cited by 61 publications

(43 citation statements)

References 15 publications

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“…In spite of that the related structures of multi-substituted coumarin are extensively studied [3][4][5]. The molecular structure of the title compound has not been reported yet.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C₁₉H₁₇IO₇

Wang

2016

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1452243The crystal structure is shown in the gure. Tables 1-3 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialTo a stirred water solution (30 mL) of sodium carbonate (1.06 g, 10.0 mmol) was added a THF solution (10 mL) of 4-hydroxy-5-methoxy-7-(methoxy)-2H-chromen-2-one (1.26 g, 5.0 mmol). After stirring at room temperature for 15 min,

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“…In spite of that the related structures of multi-substituted coumarin are extensively studied [3][4][5]. The molecular structure of the title compound has not been reported yet.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C₁₉H₁₇IO₇

Wang

2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…The coumarin dye DMB was synthesized according to the literature [16] and its molecular structure is shown in Fig. 1.…”

Section: Methodsmentioning

confidence: 99%

Fluorescence Quenching of DMB by Aniline in Benzene-Acetonitrile Mixture

Sidarai

Desai

Hunagund

et al. 2016

ILCPA

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Keywords: Fluorescence quenching, sphere of action static quenching model, finite sink approximation model. Abstract.The fluorescence quenching of coumarin dye namely 4-(2, 6-dibromo-4-methylphenoxymethyl)-benzo[h]chromen-2-one [DMB] has been studied by aniline, in a different solvent mixture of benzene (BN) and acetonitrile (AN) at room temperature. The quenching is found to be appreciable and shows positive deviation from linearity in the Stern-Volmer (S-V) plots for all the solvent mixtures. The various rate parameters responsible for fluorescence quenching have been determined using a sphere of action static quenching model and finite sink approximation model. The magnitudes of these rate parameters indicate that positive deviation in the S-V plot is due to both static and dynamic quenching processes.

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“…They also form the core of several molecules of pharmaceutical importance. Coumarin and its derivatives have been reported to serve as anti-bacterial (Basanagouda et al, 2009), anti-oxidant (Vukovic et al, 2010) and antiinflammatory agents (Emmanuel-Giota et al, 2001). In view of their importance and as a continuation of our work on the crystal structure analysis of coumarin derivatives (Abou et al, 2012(Abou et al, , 2013, we report herein the synthesis, crystal structure and Hirshfeld surface analysis of the title compound.…”

Section: Structure Descriptionmentioning

confidence: 99%

2-Oxo-2H-chromen-7-yl 4-methylbenzoate

Djandé

Abou²,

Kini

et al. 2018

IUCr Data

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In the title compound, C 17 H 12 O 4 , the benzoate ring is oriented at an acute angle of 60.14 (13) relative to the coumarin plane (r.m.s. deviation = 0.006 Å ). This conformation is stabilized by an intramolecular C-HÁ Á ÁO weak hydrogen bond, which forms a five-membered ring. Also present are -stacking interactions between neighbouring pyrone and benzene rings [centroid-to-centroid distances in the range 3.6286 (1)-3.6459 (1) Å ] and C OÁ Á Á interactions [OÁ Á Ácentroid distances in the range 3.2938 (1)-3.6132 (1) Å ]. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions. Structure descriptionCoumarins and their derivatives constitute one of the major classes of naturally occurring compounds and interest in their chemistry continues unabated because of their usefulness as biologically active agents. They also form the core of several molecules of pharmaceutical importance. Coumarin and its derivatives have been reported to serve as anti-bacterial (Basanagouda et al., 2009), anti-oxidant (Vukovic et al., 2010 and antiinflammatory agents (Emmanuel-Giota et al., 2001). In view of their importance and as a continuation of our work on the crystal structure analysis of coumarin derivatives (Abou et al., 2012(Abou et al., , 2013, we report herein the synthesis, crystal structure and Hirshfeld surface analysis of the title compound.The molecular structure of the title compound is illustrated in Fig. 1. In this structure, an S(5) ring motif arises from an intramolecular C16-H16Á Á ÁO3 hydrogen bond IUCrData (2018). 3, x180927 data reports (Table 1), and generates a pseudo bicyclic ring system (Fig. 1). The coumarin ring system is planar [r.m.s. deviation = 0.006 Å ] and is oriented at an acute angle of 60.14 (13) with respect to the C11-C16 benzene ring, while the angles between the pseudo five-membered ring [r.m.s deviation = 0.007 Å ] and the coumarin ring system and C11-C16 benzene ring are 60.91 (12) and 1.06 (15) , respectively. These dihedral angles show that the five-membered hydrogen-bonded ring and the C11-C16 benzene ring are almost coplanar. Also, an inspection of the bond lengths shows that there is a slight asymmetry of the electron distribution around the pyrone ring: the C2-C3 [1.336 (5) Å ] and C1-C2 [1.446 (5) Å ] bond lengths are shorter and longer, respectively, than those excepted for a C ar -C ar bond. This feature suggests that the electron density is preferentially located on the C2-C3 bond of the pyrone ring, as seen in other coumarin derivatives (e.g. Gomes et al., 2016;Ziki et al., 2016).In the crystal, no intermolecular hydrogen bonds are observed. The unique close intermolecular contacts present are O2Á Á ÁH17A and C4Á Á ÁC1, with distances shorter than the sum of the van der Waals radii [O2Á Á ÁH17A(x, Ày, 1 2 + z) = 2.65 and C4Á Á ÁC1 (x, y À 1, z) = 3.364 (5) Å ], and unusual C1 O2Á Á Á interactions [O2Á Á ÁCg1 (x, 1 + y, z) = 3.294 (3), O2Á Á ÁCg4(x, 1 + y, z) = 3.613 (3) Å , where Cg1 and Cg4 are respectively the centroids of the pyrone ri...

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Synthesis of some new 4-aryloxmethylcoumarins and examination of their antibacterial and antifungal activities

Cited by 61 publications

References 15 publications

Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C₁₉H₁₇IO₇

Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C₁₉H₁₇IO₇

Fluorescence Quenching of DMB by Aniline in Benzene-Acetonitrile Mixture

2-Oxo-2H-chromen-7-yl 4-methylbenzoate

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Synthesis of some new 4-aryloxmethylcoumarins and examination of their antibacterial and antifungal activities

Cited by 61 publications

References 15 publications

Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C19H17IO7

Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C19H17IO7

Fluorescence Quenching of DMB by Aniline in Benzene-Acetonitrile Mixture

2-Oxo-2H-chromen-7-yl 4-methylbenzoate

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Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C₁₉H₁₇IO₇

Crystal structure of 3-iodo-5-methoxy-7-(methoxymethoxy)-4-(3-methoxyphenoxy)-2H-chromen-2-one, C₁₉H₁₇IO₇