02892nas a2200241 4500008004100000022001400041245015700055210006900212260009400281300001200375490000700387520187800394653004302272653002802315653003202343653002302375653002802398100002402426700002202450700002302472700002502495856013002520 2016 eng d a1741-599300aCrystal structure, computational studies, and stereoselectivity in the synthesis of 2-aryl-thiazolidine-4-carboxylic acids via insitu imine intermediate0 aCrystal structure computational studies and stereoselectivity in a2-4 PARK SQUARE, MILTON PARK, ABINGDON OR14 4RN, OXON, ENGLANDbTAYLOR & FRANCIS LTDcMAR a401-4250 v373 a

This article presents the synthesis of (2R/2S,4R)-2-aryl-thiazolidine-4-carboxylic acids via nucleophilic addition of L-Cysteine on aromatic aldehydes involving a yield and time-effective room temperature reaction in an aqueous DMSO medium in the presence of NaHCO3 as a base. The synthesized diastereomers were spectroscopically characterized and quantified for diastereomeric excess by liquid chromatography-mass spectrometry analysis. The impact of the type and position of substituent in aromatic aldehydes on reaction time, % yield, H-1 NMR shift at newly formed chiral center [C(2)-H], and diastereomeric excess (de%) have been investigated. A plausible mechanism for stereoselectivity via an in situ imine intermediate is proposed using real-time IR monitoring of the synthetic reaction based on the significant signals at 1597, 1593cm(-1) for imine (C=N) stretching. The imine mechanism for stereoselectivity was further supported by NMR studies of azomethine C-13 NMR signals at 159, 160ppm and by the single crystal structure of hitherto unknown (2S,4R)-3-(tert-butoxycarbonyl)-2-(2-hydroxyphenyl)thiazolidine-4-carbox ylic acid (3a) obtained as a major diastereomer in the synthesis of the butyloxy carbonyl (BOC) derivative of (2R/2S,4R)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid. The significant ortho-OH effect of phenolic hydroxyl group leading to strong hydrogen bondings plays a vital role in the formation of 2S,4R BOC derivative stereoselectively. The frontier molecular orbitals, possible electronic excitations, IR band characterizations, and reactivity parameters of newly reported compound (3a) have been predicted using quantum chemical descriptors from density functional theory. The theoretical exploration of experimental spectra using time-dependent DFT indicated a (-*) transition between HOMO and LUMO in the ultraviolet region.

10a2-aryl-thiazolidine-4-carboxylic acids10adensity function theory10afrontier molecular orbitals10aimine intermediate10aX-ray crystal structure1 aJagtap, Rohidas, M.1 aRizvi, Masood, A.1 aDangat, Yuvraj, B.1 aPardeshi, Satish, K. uhttp://library.ncl.res.in/content/crystal-structure-computational-studies-and-stereoselectivity-synthesis-2-aryl-thiazolidine02238nas a2200265 4500008004100000022001400041245018100055210006900236260000800305300001200313490000900325520124500334653003701579653003101616653002601647653001801673653002801691100002201719700001801741700001901759700002201778700001901800700002401819856012901843 2019 eng d a0022-286000aSynthesis, characterization, Hirshfeld surface, cytotoxicity, DNA damage and cell cycle arrest studies of N, N-diphenyl-N `-(biphenyl-4-carbonyl/4-chlorobenzoyl) thiocarbamides0 aSynthesis characterization Hirshfeld surface cytotoxicity DNA da cJUN a333-3440 v11863 a

The condensation reaction of biphenyl-4-carbonyl isothiocyanate/4-chlorobenzoyl isothiocyanate with diphenylamine yielded two new compounds; N-diphenyl-N'-(biphenyl-4-carbonyl) thiocarbamide (1) and N, N-diphenyl-N'-(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.

10aDNA damage and cell cycle arrest10aHirshfeld surface analysis10aIn vitro cytotoxicity10aThiocarbamide10aX-ray crystal structure1 aPandey, Sunil, K.1 aPratap, Seema1 aRai, Sunil, K.1 aMarverti, Gaetano1 aKaur, Manpreet1 aJasinski, Jerry, P. uhttp://library.ncl.res.in/content/synthesis-characterization-hirshfeld-surface-cytotoxicity-dna-damage-and-cell-cycle-arrest02238nas a2200253 4500008004100000022001400041245014700055210006900202260000800271300001100279490000900290520132800299653003101627653002601658653001801684653002801702100002201730700001801752700001901770700002201789700001901811700002401830856013001854 2020 eng d a0022-286000aSynthesis, characterisation, Hirshfeld surface and in vitro cytotoxicity evaluation of new N-aryl-N `-Alkoxycarbonyl thiocarbamide derivatives0 aSynthesis characterisation Hirshfeld surface and in vitro cytoto cFEB a1272690 v12023 a

Four new compounds N-(4-nitrophenyl)-N'-(isobutoxycarbonyl) thiocarbamide (1), N-(2, 4-nitrophenyl)-N'-(isobutoxycarbonyl) thiocarbamide (2), N-(4-nitrophenyl)-N'-(ethoxycarbonyl) thiocarbamide (3) and N-(2-Chloro- 4-nitrophenyl)-N'-(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.

10aHirshfeld surface analysis10aIn vitro cytotoxicity10aThiocarbamide10aX-ray crystal structure1 aPandey, Sunil, K.1 aPratap, Seema1 aRai, Sunil, K.1 aMarverti, Gaetano1 aKaur, Manpreet1 aJasinski, Jerry, P. uhttp://library.ncl.res.in/content/synthesis-characterisation-hirshfeld-surface-and-vitro-cytotoxicity-evaluation-new-n-aryl-n