- NSCLC structure-activity relationship (sar) study of diisothiocyanates for antiproliferative activity on A549 Human non-small cell lung carcinoma (NSCLC)
-
Isothiocyanate functional group (-N=C=S) is widely accepted as an important moiety for anti-cancer effects of naturally occurring isothiocyanate compounds (ITCs). Herein, a series of diisothiocyanate (diITCs) derivatives were synthesized and evaluated in antiproliferative assays on A549 human non-small cell lung cancer and IMR90 human foetal lung cell lines for structure-activity relationship (SAR) and cancer cell selectivity studies. Results showed that aliphatic and benzylic diITCs were more cytotoxic to A549 cells than natural ITCs; benzyl isothiocyanate (BITC) and phenyl isothiocyanate (PITC), and a currently available anticancer drug; etoposide. Aromatic diITCs were not as active. Notably, most of the diITCs reported in this work were significantly more selective than etoposide to inhibit proliferation of the cancer cells (A549) over the normal cells (IMR90). This study demonstrated a guideline to modify chemical structures of diITCs for anti-NSCLC agents.
- Chatwichien, Jaruwan,Prachavna, Buntarika,Suntivich, Rinrada,Kumphune, Sarawut
-
p. 569 - 574
(2019/08/07)
-
- Isothiocyanation of amines using the Langlois reagent
-
The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.
- Liao, Yan-Yan,Deng, Jian-Chao,Ke, Yan-Ping,Zhong, Xiao-Lin,Xu, Li,Tang, Ri-Yuan,Zheng, Wenxu
-
supporting information
p. 6073 - 6076
(2017/07/10)
-
- New insights into dihydrogenphosphate recognition with dirhenium(i) tricarbonyl complexes bridged by a thiourea moiety
-
Three thiourea bridged 2,2′-bipyridine ligands bearing either a single thiourea group (L1), or two units separated by either a para (L2) or meta-substituted (L3) aromatic spacer, along with the corresponding bis(fac-tricarbonylrhenium(i)) complexes are reported. The three ligands all show the anticipated binding to acetate. However 1H NMR titrations reveal an unusual cooperative binding to, and selectivity for, two dihydrogenphosphate ions. The rhenium(i) complexes similarly demonstrate unusual sigmoidal titration curves, and in the case of {Re(CO)3Br} 2(μ-L1) a surprisingly strong interaction to two anions. These were further exemplified in the emissive behaviour leading to the conclusion that there is an unusual interaction with dihydrogenphosphate, giving an initial increase in the emission, followed by a decrease and a blue shift in wavelength possibly as a result of partial deprotonation. It appears that dihydrogenphosphate binds cooperatively, with the addition of a second anion enhancing the interaction of the first, probably by proton transfer; this could explain the remarkable selectivity for phosphate seen with many reported anion receptors.
- Blackburn, Anna L.,Baker, Naomi C. A.,Fletcher, Nicholas C.
-
p. 18442 - 18452
(2014/05/20)
-
- A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
-
A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate by reacting with CS2 followed by elimination to form the isothiocyanate product with cyanuric acid as the desulfurylation reagent. The choice of solvent is of decisive importance for the successful formation of the dithiocarbamate salt particularly for highly electron-deficient substrates. This novel and economical method is suitable for scale-up activities.
- Sun, Nan,Li, Bin,Shao, Jianping,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
-
experimental part
p. 61 - 70
(2012/04/04)
-
- Synthesis and antifungal activities of phenylenedithioureas
-
A total of 20 new phenylenedithiourea derivatives was synthesized by reaction of phenylenediisothiocyanates with aromatic amines as aminobenzoic, aminosalicylic acid and their derivatives. Their chemical structures were confirmed by elemental analysis, IR spectrometry and 1H NMR. The compounds were screened for in vitro antifungal, antibacterial activities and some of them have strong antifungal activities comparable to the activity observed for ketoconazole.
- Phuong, Truong,Khac-Minh, Thai,Van Ha, Nguyen Thi,Ngoc Phuong, Huynh Thi
-
p. 653 - 656
(2007/10/03)
-
- A facile one-pot preparation of isothiocyanates from aldoximes
-
Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.
- Kim, Jae Nyoung,Jung, Keum Shin,Lee, Hong Jung,Son, Ji Suk
-
p. 1597 - 1598
(2007/10/03)
-
- A FACILE NEW METHOD FOR THE PREPARATION OF AROMATIC DIISOTHIOCYANATES
-
In the present communication we describe a new facile method for the preparation of aromatic diisothiocyanates.The main advantage of this method is a one-pot procedure from bis(dithiocarbamates) compared with the methods described in the literature.
- Garin, J.,Melendez, E.,Merchan, F.,Merino, P.,Tejero, T.
-
p. 289 - 290
(2007/10/02)
-
- Fragmentation of N-aryl- and N-Aralkyl-N',N"-dicarbomethoxyguanidines with Thiophosgene
-
N-Aryl- and N-aralkyl-N',N"-dicarbomethoxyguanidines (3) on treatment with thiophosgene undergo fragmentation to yield N,N'-dicarbomethoxyurea (5) and the isothiocyanates.
- Viswanathan, N.,Sidhaye, A. R.
-
p. 659 - 660
(2007/10/02)
-
- Synthesis of Substituted Thiocarboxamides, Carboxamides and Thioureas as Potential Anthelmintic and Antimicrobial Agents
-
A series of substituted thiocarboxamides (6-26), carboxamides (27-32), thioureas (33-37) and urea (38) have been synthesized starting from various aryl isothiocyanates (1-5).Their anthelmintic and antimicrobial activities are reported.Of these 8 and 9 show 60-70percent reduction in worms at a dose of 100-250 mg/kg given for three days.
- Abuzar,Syed,Sharma, Satyavan
-
p. 230 - 233
(2007/10/02)
-
