4430-47-1Relevant academic research and scientific papers
A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide
Kuotsu, Neivotsonuo Bernadette,Jamir, Latonglila,Phucho, Tovishe,Sinha, Upasana Bora
, p. 832 - 841 (2018/01/17)
A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.
Multiple binding modes of isothiocyanates that inhibit macrophage migration inhibitory factor
Spencer, Emma S.,Dale, Edward J.,Gommans, Aimée L.,Rutledge, Malcolm T.,Vo, Christine T.,Nakatani, Yoshio,Gamble, Allan B.,Smith, Robin A.J.,Wilbanks, Sigurd M.,Hampton, Mark B.,Tyndall, Joel D.A.
, p. 501 - 510 (2015/04/27)
Macrophage migration inhibitory factor (MIF) is a pleiotropic cytokine that has roles in the innate immune response, and also contributes to inflammatory disease. While the biological properties of MIF are closely linked to protein-protein interactions, M
Synthesis and structure-activity relationship of non-peptidic antagonists of neuropilin-1 receptor
Liu, Wang-Qing,Megale, Valentino,Borriello, Lucia,Leforban, Bertrand,Montes, Matthieu,Goldwaser, Elodie,Gresh, Nohad,Piquemal, Jean-Philip,Hadj-Slimane, Reda,Hermine, Olivier,Garbay, Christiane,Raynaud, Francoise,Lepelletier, Yves,Demange, Luc
, p. 4254 - 4259 (2014/09/29)
Neuropilins (NRPs) are VEGF-A165 co-receptors over-expressed in tumor cells, and considered as targets in angiogenic-related pathologies. We previously identified compound 1, the first non-peptidic antagonist of the VEGF-A165/NRP binding, which exhibits in vivo anti-angiogenic and anti-tumor activities. We report here the synthesis and biological evaluations of new antagonists structurally-related to compound 1. Among these molecules, 4a, 4c and 4d show cytotoxic effects on HUVEC and MDA-MB-31 cells, and antagonize VEGF-A165/NRP-1 binding. This study confirmed our key structure-activity relationships hypothesis and paved the way to compound 1 'hit to lead' optimization.
ISOTHIOCYNATES AND GLUCOSINOLATE COMPOUNDS AND ANTI-TUMOR COMPOSITIONS CONTAINING SAME
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Paragraph 0094; 0096; 0110, (2013/05/21)
The present invention provides glucosinolate and isothiocyanate compounds and related methods for synthesizing these compounds and analogs. In certain embodiments, these glucosinolate and isothiocyanate compounds are useful and chemopreventive and or chemotherapeutic agents.
Synthesis and cytotoxic evaluation of quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or N-methyldithiocarbamate side Chains
Cao, Sheng-Li,Xu, Hong,Wang, Yao,Liao, Ji,Zhang, Jing-Jing,Li, Zhong-Feng,Guo, Yan-Wen,Li, Xiao-Rong,Cui, Xue-Mei,Xu, Xingzhi
experimental part, p. 163 - 173 (2012/07/31)
We have previously found that the dithiocarbamate derivatives of quinazolin-4(3H)-one could act as cytotoxic agents against a panel of human tumor cell lines. To investigate the contribution of dithiocarbamate moiety to the cytotoxic activity, three series of novel quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or Nmethyldithiocarbamate side chains were synthesized and tested for their cytotoxic activity against human cancer cell lines A549, MCF-7, HeLa, HT29 and HCT-116 by MTT assay. The results showed that transformation of the dithiocarbamate moiety in lead compound I to thiocarbamate or thiourea led to a decrease or loss of cytotoxic activity. Some N-alkylated analogs of lead compound II preferentially inhibited the proliferation of A549 cells, although their potencies were not improved in comparison with the unalkylated counterparts. The structure-activity relationship obtained in this research will be beneficial for further synthesis and discovery of effective cytotoxic agents.
Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2
Jamir, Latonglila,Sinha, Upasana Bora,Nath, Jayashree,Patel, Bhisma K.
experimental part, p. 951 - 958 (2012/02/01)
An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.
Synthesis and reactivity studies of a new reagent, ethyltriphenylphosphonium tribromide
Jamir, Latonglila,Alimenla,Kumar, Anil,Sinha, Dipak,Sinha, Upasana B.
, p. 147 - 155 (2011/03/17)
A new reagent, ethyltriphenyl phosphonium tribromide (ETPPTB), has been synthesized and studied. Results show that the reagent is quite efficient for various reactions such as organic bominations, acylations, and isothiocyanate preparation. Copyright
Efficient preparation of isothiocyanates from dithiocarbamates using bromineless brominating reagent
Yella, Ramesh,Ghosh, Harisadhan,Murru, Siva,Sahoo, Santosh K.,Patel, Bhisma K.
experimental part, p. 2083 - 2096 (2010/08/19)
For the first time, the crystal structure of a ditribromide reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been determined. Utilizing this thiophilic bromineless brominating agent EDPBT, highly useful synthetic intermediates (alkyl and aryl isothiocyanates) have been achieved directly from dithiocarbamates. EDPBT can be easily prepared from readily available reagents. It has been used as a thiophilic reagent, and its thiophilicity dominates over its brominating ability for substrates amenable to bromination. This is a sustainable process for the preparation of isothiocyantes because the spent reagent can be recovered, regenerated, and reused. Copyright Taylor & Francis Group, LLC.
The thiocarbonyl 'S' is softer than thiolate 'S': A catalyst-free one-pot synthesis of isothiocyanates in water
Jamir, Latonglila,Ali, Abdur Rezzak,Ghosh, Harisadhan,Chipem, Francis A. S.,Patel, Bhisma K.
supporting information; experimental part, p. 1674 - 1678 (2010/07/04)
Treatment of the preformed or the in situ generated aryl/alkyl dithiocarbamates triethylammonium salt (ArNHCSS-.Et 3NH+) with methyl acrylate in an aqueous medium gave solely arylisothiocyanate (ArNCS), whereas the in situ generated aryl dithiocarbamic acid (ArNHCSS-.H+) yielded exclusively the thia-Michael adduct (ArNHCSSCH2CH2COOMe). This differential reactivity can be explained by two alternative mechanisms which is dependent both on the nature of the counter cation and on the pH of the reaction medium. Irrespective of the counter cations, the thiocarbonyl sulfur (=S) atom, having large orbital-coefficient, is softer compared to the thiol/thiolate sulfur (-SH/S-) in a dithiocarbamate salt and the former adds to the Michael acceptor by a 1,4-addition.
A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
Nath, Jayashree,Patel, Bhisma K.,Jamir, Latonglila,Sinha, Upasana Bora,Satyanarayana
experimental part, p. 1503 - 1506 (2010/05/18)
An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.
