- Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent
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Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.
- Janczewski, ?ukasz,Kolesińska, Beata,Kr?giel, Dorota
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- NSCLC structure-activity relationship (sar) study of diisothiocyanates for antiproliferative activity on A549 Human non-small cell lung carcinoma (NSCLC)
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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
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p. 569 - 574
(2019/08/07)
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- Direct, Microwave-Assisted Synthesis of Isothiocyanates
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A microwave-assisted desulfuration of readily available dithiocarbamates, formed in situ from primary amines, leading to target isothiocyanates has been developed. This efficient protocol provides a rapid, environmentally benign route to aliphatic and aromatic isothiocyanates.
- Janczewski, ?ukasz,Gajda, Anna,Gajda, Tadeusz
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supporting information
p. 2528 - 2532
(2019/04/03)
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- A sulfur key Lian Niao multifunctional synergistic antioxidant stabilizer preparation method
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The invention relates to a preparation method of a multi-functional synergetic anti-oxidative stabilizer for sulfide bond linked urea. The preparation method comprises the following steps: (1) adding organic amine into CS2 and alkali to react; adding meth
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Paragraph 0063; 0064; 0065; 0066; 0067
(2017/05/12)
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- A thiourea-functionalized metal-organic macrocycle for the catalysis of Michael additions and prominent size-selective effect
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A discrete tetranuclear thiourea-based metal-organic macrocycle (MOM) with a large size was constructed by a well-designed organic ligand and nickel(ii) ions via self-assembly. Incorporating thiourea groups as hydrogen-bond donors into a metal-organic com
- Yang, Lu,Zhao, Liang,Zhou, Zhen,He, Cheng,Sun, Hui,Duan, Chunying
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p. 4086 - 4092
(2017/03/30)
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- A biological alkali dimer derivative products and method for preparing same
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The invention belongs to the technical field of applications of alkaloids to asymmetric organocatalysis and particularly relates to an alkaloid dipolymer derivative product and a preparation method thereof. An alkaloid dipolymer derivative is formed by in
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Paragraph 0071
(2017/02/24)
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- Design and synthesis of novel C2-symmetric bis-cinchona alkaloid derivatives
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Background: The commercially available dimeric cinchona alkaloids based on C-9 ether bond connecting are limited by the absence of Bronsted acid moiety and cannot meet the enantioselectivity demand. Objective: In this study, a family of novel C2/sub
- Qin, Mingkun,Gao, Mingxiang,Li, Jiangtao,Jiang, Zhiyong,Yan, Lin
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p. 446 - 449
(2016/10/18)
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- A thiourea multifunctional synergistic antioxidant stabilizer and its preparation method and application
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The invention relates to a multi-functional synergetic anti-oxidative stabilizer for thiourea as well as a preparation method and application thereof. The multi-functional synergetic anti-oxidative stabilizer has a structure shown in the specification, wh
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Paragraph 0075-0079
(2017/01/31)
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- NEW CHEMICAL COMPOUNDS
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The present invention enco mpasses co mpounds o f general formula (1) wherein R1, M1, L1 and Q are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or anomalous cell prolif
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Page/Page column 39
(2008/06/13)
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- Synthesis and antifungal activities of phenylenedithioureas
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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
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p. 653 - 656
(2007/10/03)
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- Polythioureas: Main chain chiral polymers in hydride transfer hydrogenation
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Chiral polythioureas have been synthesized and tested in asymmetric hydride transfer reduction of ketones with ruthenium. With polyurea 18, 70% ee was attained for acetophenone reduction; after filtration, it can be reused at least four times without any detectable loss of activity and only a slight decrease in selectivity. Various aryl alkyl ketones were reduced with the same system and up to 84% ee was measured with isopropyl phenyl ketone.
- Touchard, Fran?ois,Fache, Fabienne,Lemaire, Marc
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p. 3787 - 3792
(2007/10/03)
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- A FACILE NEW METHOD FOR THE PREPARATION OF AROMATIC DIISOTHIOCYANATES
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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.
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p. 289 - 290
(2007/10/02)
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- Electrophilic derivatives of purines as irreversible inhibitors of A1 adenosine receptors
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Functionalized congeners derived from 1,3-dipropyl-8-phenylxanthine and from N6-phenyladenosine were derivatized to contain electrophilic groups (isothiocyanate, N-hydroxysuccinimide ester, maleimide, sulfonyl chloride, or α-haloacyl group) capable of reaction with nucleophiles on biopolymers. The goal was to inhibit chemically the A1 adenosine receptor by using reactive agonist and antagonist ligands. Some of the electrophilic derivatives were synthesized through acylation of amine-functionalized congeners using hetero- or homobifunctional reagents available for protein cross-linking. The affinity for A1 adenosine receptors was evaluated in competitive binding assays by using rat and bovine brain membranes. Several xanthine and adenosine thiourea derivatives prepared from 1,3- and 1,4-phenylene diisothiocyanate (DITC) were potent irreversible inhibitors of adenosine receptors. Derivatives of m-DITC, at concentrations between 10 and 500 nM, irreversibly eliminated binding at 90% of the A1-receptor sites. Receptor affinity of both xanthine and adenosine derivatives containing distal phenylthiourea substituents was diminished by electron-donating groups on the ring.
- Jacobson,Barone,Kammula,Stiles
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p. 1043 - 1051
(2007/10/02)
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