@article { ISI:000297737900020, title = {Synthesis and structural characterization of homochiral homo-oligomers of parent CIS- and trans-furanoid-beta-amino acids}, journal = {Chemistry-A European Journal}, volume = {17}, number = {46}, year = {2011}, month = {NOV}, pages = {12946-12954}, publisher = {WILEY-V C H VERLAG GMBH}, address = {PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY}, abstract = {

The synthesis of homochiral homo-oligomers of cis- and trans-3-aminotetrahydrofuran-2-carboxylic acids (parent cis- and trans-furanoid-beta-amino acids, referred to as {\textquoteleft}{\textquoteleft}cis-/trans-FAA{\textquoteright}{\textquoteright}) has been carried out to understand their secondary structures and their dependence on the ring heteroatom. The oligomers of two diastereomers have been shown to have a distinct left-handed helicity. The cis-FAA homo-oligomers show a 14-helix structure, in contrast to the homo-oligomers of cis-ACPC, which adopt a sheet like structure. The trans-FAA homo-oligomers were found to adopt a 12-helix structure, the same trend found in trans-ACPC homo-oligomers. With the help of ab initio calculations, the structural features of cis-ACPC and cis-FAA hexamers were compared. We believe that the more compact packing of the cis-FAA hexapeptide should be due to a more favorable interaction between the ring and the backbone amide hydrogen.

}, keywords = {ab initio calculations, Amino acids, Density functional calculations, Peptides, secondary structures}, issn = {0947-6539}, doi = {10.1002/chem.201101855}, author = {Pandey, Sunil K. and Jogdand, Ganesh F. and Oliveira, Joao C. A. and Mata, Ricardo A. and Rajamohanan, Pattuparambil R. and Ramana, Chepuri V.} } @article { ISI:000303157400022, title = {Synthesis and structural characterization of homochiral homo-oligomers of cis-gamma-methoxy-substituted cis- and trans-furanoid-beta-amino acids}, journal = {European Journal of Organic Chemistry}, number = {13}, year = {2012}, month = {MAY}, pages = {2656-2663}, publisher = {WILEY-V C H VERLAG GMBH}, address = {BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY}, abstract = {

Herein we describe the synthesis of cis-/trans-3-aminotetrahydrofuran-2-carboxylic acids (cis-/trans-FAA) having a ?-methoxy group cis to the amine. The homo-oligomers of these two diastereomeric FAAs have been prepared. Preliminary investigation of their solution secondary structures revealed that they are the same as the homo-oligomers of the parent cis-/trans-FAA with the methoxy group only being a spectator substituent.

}, keywords = {Amino acids, helical structures, Oxygen heterocycles, Peptides}, issn = {1434-193X}, doi = {10.1002/ejoc.201101424}, author = {Giri, Awadut G. and Jogdand, Ganesh F. and Rajamohanan, Pattuparampil R. and Pandey, Sunil K. and Ramana, Chepuri V.} } @article {46009, title = {Synthesis, characterization, Hirshfeld surface, cytotoxicity, DNA damage and cell cycle arrest studies of N, N-diphenyl-N {\textquoteleft}-(biphenyl-4-carbonyl/4-chlorobenzoyl) thiocarbamides}, journal = {Journal of Molecular Structure}, volume = {1186}, year = {2019}, month = {JUN}, pages = {333-344}, type = {Article}, abstract = {

The condensation reaction of biphenyl-4-carbonyl isothiocyanate/4-chlorobenzoyl isothiocyanate with diphenylamine yielded two new compounds; N-diphenyl-N{\textquoteright}-(biphenyl-4-carbonyl) thiocarbamide (1) and N, N-diphenyl-N{\textquoteright}-(4-chlorobenzoyl) thiocarbamide (2). Structure of the compounds were determined by analytical, spectroscopic (UV-Visible, FT-IR, H-1, \& C-13 NMR), powder and single-crystal X-ray diffraction methods. Hirshfeld surface analysis and their associated two dimensional fingerprint plots of compounds were used as theoretical approach to assess driving force for crystal structure formation via the intermolecular interactions in their crystal lattices. The compounds were screened for their in vitro cytotoxicity activity against a panel of five human cancer cell lines namely; cervical (2008 and C13*) and ovarian carcinoma (A2780, A2780/CP and IGROV-1). Both the compounds exhibited promising activity against cervical and IGROV-1 cancer cells whereas for the other two cell lines appreciable activities were observed. The cell cycle arrest at G(0)/G(1) phase is supported by the DNA damage and apoptosis studies of the compounds against 2008, C13* and IGROV-1 cell lines. (C) 2019 Elsevier B.V. All rights reserved.

}, keywords = {DNA damage and cell cycle arrest, Hirshfeld surface analysis, In vitro cytotoxicity, Thiocarbamide, X-ray crystal structure}, issn = {0022-2860}, doi = {10.1016/j.molstruc.2019.03.057}, author = {Pandey, Sunil K. and Pratap, Seema and Rai, Sunil K. and Marverti, Gaetano and Kaur, Manpreet and Jasinski, Jerry P.} } @article {47330, title = {Structural, Hirshfeld surface and in vitro cytotoxicity evaluation of five new N-aryl-N{\textquoteright}-alkoxycarbonyl thiocarbamide derivatives}, journal = {Phosphorus Sulfur and Silicon and the Related Elements}, volume = {195}, year = {2020}, month = {OCT }, pages = {812-820}, type = {Article}, abstract = {

Five new compounds, N-(2, 4-dichlorophenyl)-N{\textquoteright}-(methoxycarbonyl) thiocarbamide (1), N-(2, 4-dichlorophenyl)-N{\textquoteright}-(ethoxycarbonyl) thiocarbamide (2), N-(2, 4-dichlorophenyl)-N{\textquoteright}-(2, 2, 2-trichloroethoxycarbonyl) thiocarbamide (3), N-(2,4-dichlrophenyl)-N{\textquoteright}-(pentoxycarbonyl) thiocarbamide (4) and N-(4-nitrophenyl)-N{\textquoteright}-(pentoxycarbonyl) thiocarbamide (5), have been synthesized by the reaction of various alkoxy chloroformates with 2, 4-dichloroaniline/4-nitroaniline.The molecular structures of the compounds were elucidated by using spectroscopic methods (FT-IR, H-1 and C-13 NMR) and single-crystal X-ray structure analysis of compounds 2 and 5. Antiperiplanar orientation of C = O and C = S group across C-N bonds of thiocarbamide core may be due to the presence of intramolecular (N-H center dot center dot center dot O-C) hydrogen bond in the crystal structure of both the compounds. The presence of intermolecular interactions (C-H center dot center dot center dot S, C-H center dot center dot center dot O and N-H center dot center dot center dot S) in the molecular structure of the compounds has been studied in detail using Hirshfeld surfaces and their associated twodimensional fingerprint plots. In vitro cytotoxicity screening of the synthesized compounds evaluated on a panel of seven human cancer cell lines (cervical carcinoma (2008, C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1)) demonstrated significant inhibitory properties.

}, keywords = {Hirshfeld surface analysis, In vitro cytotoxicity, Thiocarbamide, X-ray crystal structure determination}, issn = {1042-6507}, doi = {10.1080/10426507.2020.1756809, Early Access Date = MAY 2020}, author = {Pandey, Sunil K. and Pratap, Seema and Rai, Sunil K. and Marverti, Gaetano} } @article {46960, title = {Synthesis, characterisation, Hirshfeld surface and in vitro cytotoxicity evaluation of new N-aryl-N {\textquoteleft}-Alkoxycarbonyl thiocarbamide derivatives}, journal = {Journal of Molecular Structure}, volume = {1202}, year = {2020}, month = {FEB}, pages = {127269}, type = {Article}, abstract = {

Four new compounds N-(4-nitrophenyl)-N{\textquoteright}-(isobutoxycarbonyl) thiocarbamide (1), N-(2, 4-nitrophenyl)-N{\textquoteright}-(isobutoxycarbonyl) thiocarbamide (2), N-(4-nitrophenyl)-N{\textquoteright}-(ethoxycarbonyl) thiocarbamide (3) and N-(2-Chloro- 4-nitrophenyl)-N{\textquoteright}-(ethoxycarbonyl) thiocarbamide (4) were prepared and their structures confirmed by using various spectroscopic (FT-IR, UV-Visible, H-1 and C-13 NMR) and single crystal X-ray studies of 1 and 3. The presence of intramolecular (N-H center dot center dot center dot O=C) hydrogen bond in the crystal structure of both the compounds causes planarity of carbonyl thiocarbamide unit and trans orientation of C=O and C=S group. The intermolecular contacts (C-H center dot center dot center dot S, C-H center dot center dot center dot O and N-H center dot center dot center dot S) present in crystal structures have been examined by Hirshfeld surface analysis and their associated 2D fingerprint plots. All the compounds were assessed for their in vitro cytotoxic properties against a panel of seven human cancer cells such as cervical carcinoma (2008, C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1). Among them, compounds 2 and 4 exhibited better activity than 1 and 3 against all the cell lines tested. (C) 2019 Elsevier B.V. All rights reserved.

}, keywords = {Hirshfeld surface analysis, In vitro cytotoxicity, Thiocarbamide, X-ray crystal structure}, issn = {0022-2860}, doi = {10.1016/j.molstruc.2019.127269}, author = {Pandey, Sunil K. and Pratap, Seema and Rai, Sunil K. and Marverti, Gaetano and Kaur, Manpreet and Jasinski, Jerry P.} }