Synthesis, Characterization, Thermal and Antimicrobial studies of N-substituted Sulfanilamide derivatives

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Synthesis, Characterization, Thermal and Antimicrobial studies of N-substituted Sulfanilamide derivatives. / Lahtinen, Manu; Kudva, Jyothi; Hegde, Poornima; Bhat, Krishna; Kolehmainen, Erkki; Nonappa; Venkatesh, Venkatesh; Naral, Damodara.

In: JOURNAL OF MOLECULAR STRUCTURE, Vol. 1060, 24.02.2014, p. 280-290.

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Lahtinen, Manu ; Kudva, Jyothi ; Hegde, Poornima ; Bhat, Krishna ; Kolehmainen, Erkki ; Nonappa ; Venkatesh, Venkatesh ; Naral, Damodara. / Synthesis, Characterization, Thermal and Antimicrobial studies of N-substituted Sulfanilamide derivatives. In: JOURNAL OF MOLECULAR STRUCTURE. 2014 ; Vol. 1060. pp. 280-290.

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@article{eb1bf83bca0041af82a2569c5cecee43,
title = "Synthesis, Characterization, Thermal and Antimicrobial studies of N-substituted Sulfanilamide derivatives",
abstract = "Four sulfanilamide derivatives N-[4-(phenylsulfamoyl)phenyl]acetamide (1), 4-amino-N-phenylben-zenesulfonamide (2), N-[4-(phenylsulfamoyl)phenyl]benzamide (3) and N-(4-[(3-chlorophenyl)sulfamoyl]phenylbenzamide (4) were synthesized and characterized by Infra-Red (IR), Nuclear Magnetic Resonance (NMR) and UV-visible (UV-Vis) spectra. Also Liquid Chromatographic (LCMS) and High Resolution Mass Spectrometric (HRMS) methods were used. Crystal structures of 1-4 were determined by single crystal X-ray diffraction (XRD) and their conformational and hydrogen bond (HB) network properties were examined with survey of the literature data. Compounds 1 and 2 crystallize in the same orthorhombic Pbca symmetry with equivalent molecular conformation (tilted V-shape) but showed distinct packing and hydrogen bonding models. Compounds 3 and 4 crystallize in monoclinic and triclinic crystal systems, albeit exhibiting identical molecular conformation (L-shaped). Same donor acceptor pairs both on 3 and 4 result to different kind of HE network. Thermogravimetric (TG) and differential scanning calorimetric (DSC) methods were used to evaluate thermal properties of the substances. All sulfanilamide derivatives have melting points between 195-227 degrees C, initiation of thermal decomposition between 259-271 degrees C and enthalpies of fusion Delta H-fus(T), = 38.96, 36.60, 46.23 and 44.81 kJ mol-1 were determined for 1-4, respectively. The derivatives were screened for their antibacterial and antifungal activities against various bacterial and fungal strains. It is observed that there is no significant antibacterial activity with the introduction of the benzene ring to CO-NH group or SO2-NH moiety, and none of the compounds exhibited antifungal activity. (C) 2013 Elsevier B.V. All rights reserved.",
keywords = "Synthesis, Sulfanilamides, Antimicrobial activity, X-ray diffraction, Crystal structure, Thermal analysis, CARBONIC-ANHYDRASE INHIBITORS, CRYSTAL-STRUCTURE, SULFONAMIDE DERIVATIVES, DESIGN, SUBLIMATION, SOLUBILITY, SOLVATION, ACID",
author = "Manu Lahtinen and Jyothi Kudva and Poornima Hegde and Krishna Bhat and Erkki Kolehmainen and Nonappa and Venkatesh Venkatesh and Damodara Naral",
year = "2014",
month = "2",
day = "24",
doi = "10.1016/j.molstruc.2013.12.063",
language = "English",
volume = "1060",
pages = "280--290",
journal = "JOURNAL OF MOLECULAR STRUCTURE",
issn = "0022-2860",
publisher = "Elsevier Science B.V.",

}

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TY - JOUR

T1 - Synthesis, Characterization, Thermal and Antimicrobial studies of N-substituted Sulfanilamide derivatives

AU - Lahtinen, Manu

AU - Kudva, Jyothi

AU - Hegde, Poornima

AU - Bhat, Krishna

AU - Kolehmainen, Erkki

AU - Nonappa, null

AU - Venkatesh, Venkatesh

AU - Naral, Damodara

PY - 2014/2/24

Y1 - 2014/2/24

N2 - Four sulfanilamide derivatives N-[4-(phenylsulfamoyl)phenyl]acetamide (1), 4-amino-N-phenylben-zenesulfonamide (2), N-[4-(phenylsulfamoyl)phenyl]benzamide (3) and N-(4-[(3-chlorophenyl)sulfamoyl]phenylbenzamide (4) were synthesized and characterized by Infra-Red (IR), Nuclear Magnetic Resonance (NMR) and UV-visible (UV-Vis) spectra. Also Liquid Chromatographic (LCMS) and High Resolution Mass Spectrometric (HRMS) methods were used. Crystal structures of 1-4 were determined by single crystal X-ray diffraction (XRD) and their conformational and hydrogen bond (HB) network properties were examined with survey of the literature data. Compounds 1 and 2 crystallize in the same orthorhombic Pbca symmetry with equivalent molecular conformation (tilted V-shape) but showed distinct packing and hydrogen bonding models. Compounds 3 and 4 crystallize in monoclinic and triclinic crystal systems, albeit exhibiting identical molecular conformation (L-shaped). Same donor acceptor pairs both on 3 and 4 result to different kind of HE network. Thermogravimetric (TG) and differential scanning calorimetric (DSC) methods were used to evaluate thermal properties of the substances. All sulfanilamide derivatives have melting points between 195-227 degrees C, initiation of thermal decomposition between 259-271 degrees C and enthalpies of fusion Delta H-fus(T), = 38.96, 36.60, 46.23 and 44.81 kJ mol-1 were determined for 1-4, respectively. The derivatives were screened for their antibacterial and antifungal activities against various bacterial and fungal strains. It is observed that there is no significant antibacterial activity with the introduction of the benzene ring to CO-NH group or SO2-NH moiety, and none of the compounds exhibited antifungal activity. (C) 2013 Elsevier B.V. All rights reserved.

AB - Four sulfanilamide derivatives N-[4-(phenylsulfamoyl)phenyl]acetamide (1), 4-amino-N-phenylben-zenesulfonamide (2), N-[4-(phenylsulfamoyl)phenyl]benzamide (3) and N-(4-[(3-chlorophenyl)sulfamoyl]phenylbenzamide (4) were synthesized and characterized by Infra-Red (IR), Nuclear Magnetic Resonance (NMR) and UV-visible (UV-Vis) spectra. Also Liquid Chromatographic (LCMS) and High Resolution Mass Spectrometric (HRMS) methods were used. Crystal structures of 1-4 were determined by single crystal X-ray diffraction (XRD) and their conformational and hydrogen bond (HB) network properties were examined with survey of the literature data. Compounds 1 and 2 crystallize in the same orthorhombic Pbca symmetry with equivalent molecular conformation (tilted V-shape) but showed distinct packing and hydrogen bonding models. Compounds 3 and 4 crystallize in monoclinic and triclinic crystal systems, albeit exhibiting identical molecular conformation (L-shaped). Same donor acceptor pairs both on 3 and 4 result to different kind of HE network. Thermogravimetric (TG) and differential scanning calorimetric (DSC) methods were used to evaluate thermal properties of the substances. All sulfanilamide derivatives have melting points between 195-227 degrees C, initiation of thermal decomposition between 259-271 degrees C and enthalpies of fusion Delta H-fus(T), = 38.96, 36.60, 46.23 and 44.81 kJ mol-1 were determined for 1-4, respectively. The derivatives were screened for their antibacterial and antifungal activities against various bacterial and fungal strains. It is observed that there is no significant antibacterial activity with the introduction of the benzene ring to CO-NH group or SO2-NH moiety, and none of the compounds exhibited antifungal activity. (C) 2013 Elsevier B.V. All rights reserved.

KW - Synthesis

KW - Sulfanilamides

KW - Antimicrobial activity

KW - X-ray diffraction

KW - Crystal structure

KW - Thermal analysis

KW - CARBONIC-ANHYDRASE INHIBITORS

KW - CRYSTAL-STRUCTURE

KW - SULFONAMIDE DERIVATIVES

KW - DESIGN

KW - SUBLIMATION

KW - SOLUBILITY

KW - SOLVATION

KW - ACID

U2 - 10.1016/j.molstruc.2013.12.063

DO - 10.1016/j.molstruc.2013.12.063

M3 - Article

VL - 1060

SP - 280

EP - 290

JO - JOURNAL OF MOLECULAR STRUCTURE

JF - JOURNAL OF MOLECULAR STRUCTURE

SN - 0022-2860

ER -

ID: 3308988