cas 5344-82-1, 1-(2-Chlorophenyl)-2-thiourea

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Discovery of aminothiazole derivatives as novel human enterovirus A71 capsid protein inhibitors
Enterovirus A71 (EV-A71), one of the major pathogens that causes hand, foot and mouth disease (HFMD), has seriously threatened the health and safety of young children. In this study, aminothiazole derivatives were synthesized and screened against EV-A71 in Rhabdomyosarcoma (RD) cells. The best compound (12s), with a biphenyl group, showed activity against EV-A71 (EC50: 0.27 μM) but also against a series of different human enteroviruses without significant cytotoxicity (CC50 > 56.2 μM). Mechanistic studies including time-of-drug-addition assays, viral entry assays and microscale thermophoresis (MST) experiments, showed that 12s binds to EV-A71 capsid and blocks the binding between the viral protein VP1 and the relevant human scavenger receptor class B member 2 (hSCARB2).
Cai, Yang,Chen, Yinuo,Dong, Chune,Lan, Ke,Lei, Ping,Tang, Qi,Wu, Shuwen,Xu, Ting,Xu, Zhichao,Zhou, Hai-Bing,Zou, Wenting
(2022/03/15)

Self-assembly of a benzothiazolone conjugate into panchromatic fluorescent fibres and their application in cellular imaging
We report the synthesis and characterization of the structures formed by self-assembly of 4-chloro-2(3H)-benzothiazolone (CBT) into panchromatic fibres and their application in cellular imaging. The aggregation properties of the synthesized compound were studied extensively under different solvents and concentrations and their morphologies examined at a supramolecular level by various microscopic techniques such as atomic force microscopy (AFM), fluorescence microscopy, and optical microscopy. Interestingly, the self-assembled structures formed byCBTreveal panchromatic emission properties and show blue, green, and red fluorescence under different excitation wavelengths. The mechanism of structure formation of the self-assemblies was studied through different techniques such as concentration-dependent1H-NMR, ATR-FTIR, UV-visible spectroscopy, and fluorescence spectroscopy. Finally, the utility ofCBTfor cell imaging applications was demonstrated and it can be noted thatCBTwas efficiently taken up by mammalian cells and the cells revealed panchromatic emission in the blue, green, and red channels. The intensities of the fluorescence observed were blue > green > red and the dye interestingly does not exhibit any fluorescence quenching.
Bhatia, Dhiraj,Gangrade, Ankit,Gour, Nidhi,Haque, Ashadul,Joshi, Khashti Ballabh,Koshti, Bharti,Kshtriya, Vivekshinh,Singh, Ramesh
p. 17211 - 17221
(2021/10/04)

Design, synthesis, and antipoliferative activities of novel substituted imidazole-thione linked benzotriazole derivatives
A new series of benzotriazole moiety bearing substituted imidazol-2-thiones at N1 has been designed, synthesized and evaluated for in vitro anticancer activity against the different cancer cell lines MCF-7(breast cancer), HL-60 (Human promyelocytic leukemia), and HCT-116 (colon cancer). Most of the benzotriazole analogues exhibited promising antiproliferative activity against tested cancer cell lines. Among all the synthesized compounds, BI9 showed potent activity against the cancer cell lines such as MCF-7, HL-60 and HCT-116 with IC50 3.57, 0.40 and 2.63 μM, respectively. Compound BI9 was taken up for elaborate biological studies and the HL-60 cells in the cell cycle were arrested in G2/M phase. Compound BI9 showed remarkable inhibition of tubulin polymerization with the colchicine binding site of tubulin. In addition, compound BI9 promoted apoptosis by regulating the expression of pro-apoptotic protein BAX and anti-apoptotic proteins Bcl-2. These results provide guidance for further rational development of potent tubulin polymerization inhibitors for the treatment of cancer.
El-Malah, Afaf,Khayyat, Ahdab N.,Malebari, Azizah M.,Mohamed, Khaled O.
(2021/10/12)

Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene
A simple, cost-effective, environmentally benign, and efficient one-pot tandem approach to the synthesis of pharmaceutically important 1-aryl-1H-tetrazole-5-amines 3a-k and 4a-k has been described. The reaction utilized 1-phenyl thiourea, which was generated in situ from aqueous ammonia and isocyanates 1a-k, for the formation of heterocumenes using sodium azide, triethylamine, and ceric ammonium nitrate (CAN) to obtain various aryl-substituted 1H-tetrazole-5-amines (3a-k) in good to excellent yields.
Kondhare, Dasharath D.,Bhadke, Venkat V.,Deshmukh, Sushma S.,Wakhradkar, Mahesh G.,Totawar, Balaji B.
(2021/07/28)

Novel compound bassed on thiazolidine and use thererof
The present invention relates to a novel compound and uses thereof. More specifically, the present invention provides: a novel compound based on thiazolidine which can effectively inhibit the aggregation of tau, one of the causes of Alzheimerandprime;s disease; and uses thereof. According to the novel compound and uses thereof composed as described above, it is possible to realize an effect of producing a therapeutic agent for Alzheimerandprime;s dementia due to tau aggregation.COPYRIGHT KIPO 2020
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Paragraph 0091-0092; 0103-0104; 0107-0108

(2020/06/06)

Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect of a 3-bromophenylamino moiety in position 3 of the triazole for both series (compounds 2.6 and 4.6) on several cell lines tested. Moreover, our results point out an antiangiogenic activity of these compounds. Overall, the 5-aryl-3-phenylamino-1,2,4-triazole structure has promising dual anticancer activity.
Benhida, Rachid,Demange, Luc,Dufies, Maeva,Grytsai, Oleksandr,Hagege, Anais,Martial, Sonia,Pagès, Gilles,Penco-Campillo, Manon,Ronco, Cyril,Valiashko, Oksana
(2020/10/02)

CuBr2 mediated synthesis of 2-Aminothiazoles from dithiocarbamic acid salts and ketones
In a one-pot procedure, CuBr2 has been used as a efficient desulfurizing agent in the synthesis of 2-aminothiazoles by the condensation of in situ-generated 1-substituted thioureas from their dithiocarbamic acid salts, with in situ-generated α-bromoketones from ketones. All reactions were carried out under optimized reaction conditions and gave the target products in 61–95% yield.
Zhang, Baohua,Shi, Lanxiang
p. 1134 - 1139
(2019/07/15)

Design, synthesis and molecular docking studies of some thiazole clubbed heterocyclic compounds as possible anti-infective agents
The present work describes synthesis of a series of 5-((1-(4-(4-chlorophenyl)thiazol-2-yl)-3- aryl-1H-pyrazol-4-yl)methylene)-2-(arylimino)thiazolidin-4-one derivatives and their molecular docking and biological evaluation as possible antimalarial, anthelmintic and antimicrobial agents. The synthesis of compounds has been accomplished by adopting suitable synthetic methods. Structures of newly synthesized compounds were characterized and authenticated by spectral methods such as IR, 1H-NMR and mass spectra. Synthesized compounds were screened for their in vitro antimicrobial activity against selected bacterial strains and fungal strains viz. B. subtilis, S. aureus, E. coli, P. fluorescens, C. albicans, C. glabrata and antimalarial studies against P. falciparum. Titled compounds were also tested against Pheretima posthuma (earthworm) for their anthelmintic activity. Molecular docking was done to study the binding modes of the potent compounds against Escherichia coli (PDB ID: 1AB4) and Candida P450DM (PDB ID: 1EA1) enzymes. The results revealed that all the compounds exhibited moderate to significant antimicrobial activities. Antimalarial activity screening revealed that one compound 8i showed significant antimalarial activity with of IC50; 0.59 μg/mL as compared to standard drugs chloroquine (IC50= 0.020 μg/mL) and quinine (IC50; 0.268 μg/mL). The most active compound exhibited the mean paralysis time of 19.2 ± 0.9 min and mean death time of 31.7 ± 2.5 min. It can be concluded that some of the synthesized compounds have remarkable antiinfective, antimalarial and anthelmintic activity and are suitable candidates for further scientific exploration.
Sharma, Prabodh Chander,Saini, Anil,Bansal, Kushal Kumar,Sharma, Archana,Gupta, Girish Kumar
p. 716 - 726
(2018/07/13)

Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors
Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents could be easily prepared by a rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or inconvenient reagents such as elemental halogens. These useful products can serve as starting materials for other reactions or as pharmacologically interesting compounds. In our work we have shown that the resulting 5-bromothiazole compounds could lead to monoacylglycerol lipase (MAGL) inhibition in the μM range.
Prevost, Julien R.C.,Kozlova, Arina,Es Saadi, Bouazza,Yildiz, Esra,Modaffari, Sara,Lambert, Didier M.,Pochet, Lionel,Wouters, Johan,Dolu?ic?, Eduard,Frédérick, Rapha?l
supporting information
p. 4315 - 4319
(2018/11/03)

A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide
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.
Kuotsu, Neivotsonuo Bernadette,Jamir, Latonglila,Phucho, Tovishe,Sinha, Upasana Bora
p. 832 - 841
(2018/01/17)

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae
A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).
Wang, Rong,Hou, Shuang,Dong, Xiaojing,Chen, Daijie,Shao, Lei,Qian, Liujia,Li, Zhong,Xu, Xiaoyong
supporting information
p. 2060 - 2066
(2017/11/22)

Synthesis and antitumor evaluation of 5-(benzo[: D] [1,3]dioxol-5-ylmethyl)-4-(tert -butyl)- N -arylthiazol-2-amines
A series of novel N-aryl-5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)thiazol-2-amines (C1-C31) were synthesized and evaluated for their antitumor activities against HeLa, A549 and MCF-7 cell lines. Some tested compounds showed potent growth inhibition properties with IC50 values generally below 5 μM against the three human cancer cells lines. Compound C27 showed potent activities against HeLa and A549 cell lines with IC50 values of 2.07 ± 0.88 μM and 3.52 ± 0.49 μM, respectively. Compound C7 (IC50 = 2.06 ± 0.09 μM) was the most active compound against A549 cell line, while compound C16 (IC50 = 2.55 ± 0.34 μM) showed the best inhibitory activity against the MCF-7 cell line. The preliminary mechanism of the inhibitory effect was investigated via further experiments, such as morphological analysis by dual AO/EB staining and Hoechst 33342 staining, and cell apoptosis and cycle assessment by FACS analysis. The results illustrated that compound C27 could induce apoptosis and cause both S-phase and G2/M-phase arrests in HeLa cell line. Therefore, compound C27 could be developed as a potential antitumor agent.
Wu,Fang,Tang,Xiao,Ye,Li,Hu
p. 1768 - 1774
(2016/09/28)

Facile synthesis, molecular docking and toxicity studies of 4-Phenyl-3-phenylamino-4H-[1,2,4]thiadiazol-5-one analogs as GABAA receptor agonists
A series of 4-Phenyl-3-phenylamino-4H-[1,2,4]thiadiazol-5-one derivatives was synthesized by a simple method and their structures were established by physical and spectroscopic methods like infrared, mass and nuclear magnetic resonance spectroscopy. Elemental formulae of all the compounds were determined by elemental analysis and compared with the calculated value. Log P value and in vitro hydrolysis, in simulated gastric fluid and simulated intestinal fluid, for all the compounds were determined by standard methods. Synthesized 1, 2, 4-thiadiazolines were screened for their anticonvulsant activity against maximal electroshock method and isoniazid induced seizures. All the compounds showed good anticonvulsant activity. The compound 4-(3,4-dichloro-phenyl)-3-(3,4-dichloro-phenylamino)-4H-[1,2,4]thiadiazol-5-one (3a) was found to be the most potent member of the series. Molecular docking studies of the synthesized compounds depicted their stable ligand–receptor complex conformation with the typical binding pocket of γ-aminobutyric acid A receptor protein. Compound 3a confined its effect in the molecular docking studies also with non-covalent interactions with Tyr 157, Phe 200 and Tyr 205, the key interacting residues of γ-aminobutyric acid A receptor protein 4COF. In silico absorption, distribution, metabolism and elimination performance of all the compounds also appear to favour anticonvulsant effect. “LAZAR” and “OSIRIS” property explorer predicted nontoxic, nonmutagenic, noncarcinogenic, etc. nature for all the compounds. In conclusion, some γ-aminobutyric acid A receptor agonists have been synthesized in this study with promising drug-like properties, which merit further development.
Diwakar, Kirti,Sonar, Pankaj Kumar,Mishra, Mudita,Tripathi, Avinash C.,Saraf, Shailendra K.
p. 2631 - 2642
(2016/10/25)

Synthesis, characterization and investigation of novel benzoyl protected glycosyl l-formamidino-3-aryl formamidino thiocarbamides for antimicrobial activity
In the present investigation, a series of novel benzoyl protected glycosyl l-formamidino-3-aryl formamidino thiocarbamides have been synthesized by interaction of various benzoyl procted glycosyl bromides and 1-aryl-formamidino-3-formamidino thiocarbamides. The required benzoyl procted glycosyl bromides have been synthesized by benzoylation followed by bromination and l-aryl-formamidino-3-formamidino thiocarbamides have been synthesized by interaction of aryl thiocarbamides and cyanoguanidine. All the newly synthesized compounds have been characterized by usual chemical transformations, elemental analysis, IR, 1H NMR and mass spectral studies. These compounds have been investigated for their potential against several human pathogenic bacteria and fungi for their antibacterial and antifungal activity against Escherichia coil, Staphylococcus aureus, Salmonella typhi and Penicilium notatum, Aspergillus Niger respectively. Some of the synthesized compounds show very promising activity.
Thakur,Deshmukh
p. 1248 - 1253
(2017/04/28)

Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists
Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.
Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Ali, Yakub,Dhulap, Abhijeet,Alam, Perwez,Pasha, M. A. Qadar
p. 354 - 362
(2016/10/19)

A new route for the synthesis of 4-arylacetamido-2-aminothiazoles and their biological evaluation
A series of 4-arylacetamido-2-amino- and 2-arylamino-1,3-thiazoles (4a-o) were synthesized in a single step in high yields from ?-bromoacetoacetanilides and thiourea/phenyl thioureas and were characterized by spectral and analytical methods. The compounds were evaluated for their in vitro antibacterial antifungal and antioxidant activities. In vitro antimicrobial evaluation of these compounds indicated their specificity towards Gram-positive species. p-Tolyl and m-chlorophenyl substituents on the arylamino moiety (compounds 4b and 4g) exhibited the lowest minimum inhibitory concentration values. The other compounds exhibited promising antimicrobial and moderate antioxidant activity.
Madhura,Revankar, Hrishikesh M.,Kulkarni, Manohar V.
p. 483 - 489
(2015/08/06)

Synthesis and Cytotoxicity in Vitro of N-Aryl-4-(Tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine
A series of novel N-aryl-4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amines were synthesized in a green way. H2O2-NaBr Brominating circulatory system was used in the synthesis of the key intermediate in a mild condition. All of the target compounds were confirmed by1H NMR and elemental analysis and tested for their cytotoxicity against two different human cancer cell lines. The cytotoxicity assay revealed that some of the title compounds showed moderate to strong cytotoxic activities. Compound 2i was the most potent compound with the IC50 values of 9 μMagainst Hela cells and 15 μMagainst Bel-7402 cells, respectively.
Ye, Jiao,Xiao, Meng-Wu,Xie, Xuan-Qing,Qiu, Shen-Yi,Dai, Ming-Chong,Li, Wan,Shen, Fang,Hu, Ai-Xi
p. 627 - 631
(2018/01/18)

Synthesis and characterization of peracetylated S-maltosyl 2-isothiobiurets and 2,4-isodithiobiurets and their in vitro antimicrobial activity
A series of S-hepta-O-acetyl-maltosyl-1-aryl-5-p-tolyl-2-isothiobiurets, S-hepta-O-acetyl-maltosyl-1-aryl-5-p-chloro-phenyl-2-isothiobiurets and S-hepta-O-acetyl maltosyl-1-aryl-5-p-tolyl-2,4-isodithiobiurets have been synthesized by the interaction of various S-hepta-O-acetyl maltosyl-1-aryl isothiocarbamides with p-tolyl isocyanate, p-chloro-phenyl isocyanate and p-tolyl isothiocyanate respectively. The required maltosyl arylisothiocarbamides are synthesized by the displacement of anomeric bromide of acetobromomaltose with aryl thiocarbamides. The identities of these newly synthesized thiomaltosides have been established on the basis of chemical transformations and IR, mass, 1H and 13C NMR spectral studies. These compounds have been screened for their antibacterial and antifungal activities against E. coli, S. aureus, Ps. aeruginosa, S. typhi, R. oligosporus and A. niger. These compounds show most promising activity towards these microorganisms.
Zade, Varsha S.,Deshmukh, Shirish P.
p. 815 - 820
(2015/06/30)

Synthesis and biological evaluation of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-ones as IKK2 inhibitors
In a search for novel molecules to treat inflammatory disorders, we identified several compounds with inhibitory action against the IKK2 enzyme using in silico methods. Based on the virtual hit of compounds 1 and 2, a novel series of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-one derivatives was designed, synthesized, and evaluated for IKK2 inhibitory activity. Among the synthesized derivatives, compounds 17f and 19f showed good IKK2 inhibitory potency, which have 4-carboxaminophenyl on the 2-furan ring and a methoxy group on the phenylimino moiety at the 2-position of the core structure. The most potent compound was 2-(2,4-dimethoxyphenyl)imino-5((5(4-carboxaminophenyl)furan-2-yl)methylene)thiazolidin-4-one (19f, IC50 = 0.94 μM), which represents a synergic effect of the two virtual hit compounds against IKK2. We also identified compounds showing inhibitory activities against interleukin (IL)-17, CCK-8, and tumor necrosis factor-alpha (TNF-α), which are NF-κB-dependent pro-inflammatory cytokine mediators.
Kim, Hee Sook,Shin, Min Jae,Lee, Byungho,Oh, Kwang-Seok,Choo, Hyunah,Pae, Ae Nim,Roh, Eun Joo,Nam, Ghilsoo
p. 2621 - 2626
(2015/11/16)

Design, synthesis and investigation on the structure-activity relationships of N-substituted 2-aminothiazole derivatives as antitubercular agents
Tuberculosis (TB) is one of the deadliest infectious diseases of all times, and its recent resurgence is a supreme matter of concern. Co-infection with HIV and, in particular, the continuous isolation of new resistant strains, makes the discovery of novel anti-TB agents a strategic priority. The research of novel agents should be driven by the accessibility of the synthetic procedure and, in particular, by the lack of cross-resistance with the drugs already marketed. Moreover, in order to shorten the duration of the therapy, and therefore decrease the rate of resistance, these molecules should be active also against the nonreplicating persistent form (NRP-TB) of the infection. The availability of an in-house small library of compounds prompted us to investigate their anti-TB activity. Two compounds, embodying a 2-aminothiazole scaffold, were found to possess a certain inhibitory activity toward Mycobacterium tuberculosis H37Rv, and therefore a medicinal chemistry campaign was initiated in order to increase the activity of the hit compounds and, especially, construct a plausible body of structure-activity relationships. The potency of the hit compound was successfully improved, and, much more importantly, some of the molecules synthesized were found to be active toward the persistent phenotype, and, also, toward a panel of resistant strains. These findings encourage further investigations around this interesting antitubercular chemotype.
Pieroni, Marco,Wan, Baojie,Cho, Sanghyun,Franzblau, Scott G.,Costantino, Gabriele
p. 26 - 34
(2014/01/06)

Synthesis of some biologically important per-O-benzoyl maltosyl isothiocarbamides and isodithiobiurets as antibacterial and antifungal agents
Several S-hepta-O-benzoyl maltosyl-1-arylisothiocarbamides have been synthesized through several steps viz. benzoylation, bromination and interaction of hepta-O-benzoyl maltosyl bromide with aryl thiocarbamides. S-Hepta-Obenzoyl maltosyl-1-aryl-5-phenyl-2, 4 isodithiobiurets have been synthesized by the interaction of S-hepta-O-benzoyl maltosyl-1-arylisothiocarbamides with phenyl isothiocyanate. All new compounds have been characterized by spectral analysis such as IR, 1H NMR and mass spectra as well as elemental analysis and in-vitro antimicrobial activity of maltosyl isothiocarbamides and related isodithiobiurets has been evaluated against several human pathogens. Out of 12 compounds prepared and screened, four compounds have shown significant activity against different human pathogens.
Karhe, Usha W.,Deshmukh, Shirish P.
p. 212 - 217
(2014/03/21)

Synthesis, cytotoxic evaluation, and in silico studies of substituted N-alkylbromo-benzothiazoles
In efforts to develop a new class of anticancer agents with improved efficacy and selective action, a series of N-alkylbromo-benzothiazoles were synthesized and evaluated for in vitro cytotoxic activity against various human cancer cell lines such as lung (A-549), prostate (PC-3), leukemia (THP-1), and colon (Caco-2). They were found to be highly active against prostate (PC-3) and leukemia (THP-1) cancer cells, moderately active against colon (Caco-2) cancer cells and less active against lung (A-549) cancer cells. Of the 12 compounds, two (11d, 11j) exhibit IC50 values of ≤ 1 μM against leukemia (THP-1) cancer cell lines. Compound 11l showed significant cytotoxic activity against the PC-3 (IC50 = 0.6 μM), THP-1 (IC50 = 3 μM) and Caco-2 cell lines (IC50 = 9.9 μM), respectively. Docking study of the synthesized ligand was done on epidermal growth factor receptor using ArgusLab flexible docking, to determine their observed activity. Further QSAR investigations with stepwise multiple linear regression analysis were applied to find correlation between various physicochemical parameters and anticancer activity. The QSAR results showed that anticancer activity could be modeled with descriptors. The predictive ability of models was cross-validated by observation of the low residual activity values and adjusted coefficient of variation (radj2) obtained by leave-one-out technique.
Gill, Rupinder Kaur,Singh, Gagandeep,Sharma, Anuradha,Bedi,Saxena
p. 4211 - 4222
(2013/09/02)

Design and synthesis of N-Aryl isothioureas as a novel class of gastric H+/K+-ATPase inhibitors
To find new H+/K+-ATPase inhibitors for the treatment of peptic ulcer disease, a series of novel N-aryl isothiourea derivatives were synthesized and their structures were identified by 1H NMR and GC-MS. The effects of these compounds on inhibiting gastric acid secretion were evaluated by the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. The results showed that, of the 37 N-aryl isothiourea compounds synthesized, 20 compounds have comparable or stronger gastric acid inhibitory activities than that of pantoprazole magnesium. The quantitative structure-activity relationships (QSARs) of the N-aryl isothiourea compounds were also studied by comparative molecular field analysis (CoMFA) computation, and the model structure that was supposed to give more powerful bioactivities was finally predicted. A series of novel N-aryl isothiourea derivatives were synthesized and evaluated for their effects of inhibiting gastric acid secretion using the guinea pig stomach mucous membrane study with pantoprazole magnesium as a positive control. Compounds 2c, 2e, and 2k have higher bioactivity. The quantitative structure-activity relationships also defined these structural requirements.
Ma, Chao,Wu, Anhui,Wu, Yongqi,Ren, Xuhong,Cheng, Maosheng
p. 891 - 900
(2014/01/06)

Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2
An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.
Jamir, Latonglila,Sinha, Upasana Bora,Nath, Jayashree,Patel, Bhisma K.
p. 951 - 958
(2012/02/01)

Antiviral Compounds
Novel compounds, methods, and compositions for treating various viral infections are described. In some embodiments the novel compounds of the invention are 3-oxo-phenothiazine derivatives; more specific embodiments include 3-oxo-phenothiazine derivatives having substituents at the 1-, 7-, and 9-positions of the phenothiazine parent ring. In other embodiments, the invention provides compositions and methods for treating viral infections, especially HIV.
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(2012/09/25)

Bromineless bromine as an efficient desulfurizing agent for the preparation of cyanamides and 2-aminothiazoles from dithiocarbamate salts
In a one-pot procedure, bromineless brominating reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been used as a desulfurizing agent in the preparation of organic cyanamides and substituted thiazoles starting from dithiocarbamic acid salts. In this approach, alkyl/aryl isothiocyantes were first obtained by the desulfurization of dithiocarbamic acid salts with EDPBT. The in situ-generated isothiocyanates reacts with an aqueous ammonia, forming alkyl or aryl thioureas, which on subsequent oxidative desulfurization with EDPBT led to the formation of corresponding cyanamides in good yields. Alternatively, an efficient one-pot synthesis of substituted thiazoles has been achieved by the condensation of the in situ-generated 1-aryl thioureas with the in situ-generated -bromoketones from ketones, again using EDPBT. The reagent EDPBT can be easily prepared from the readily available reagents. Desulfurizing ability dominates over its brominating ability for substrates amenable to bromination.
Yella, Ramesh,Kavala, Veerababurao,Patel, Bhisma K.
experimental part
p. 792 - 805
(2011/04/22)

Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem
In this work, 4H-1,4-benzothiazines were synthesized by an efficient synthetic method in a single step involving heterocyclization of substituted 2-aminobenzenethiols with β-ketoester. The structures of the synthesized compounds were confirmed by their analytical and spectral data. The synthesized compounds were evaluated for their antimicrobial activity against bacterial species; E. coli and Bacillus cereus. The synthesized compounds showed significant activity against microorganisms, which can be correlated with the privileged heterocyclic structural scaffolds.
Sharma, Praveen Kumar,Fogla, Ankur,Rathore,Kumar
experimental part
p. 1103 - 1111
(2012/04/17)

Tandem regioselective synthesis of tetrazoles and related heterocycles using iodine
A one-pot, tandem process has been developed for the synthesis of a library of tetrazoles from aryl isothiocyanates. Condensation of aryl isothiocyanates with ammonia, and aryl amines (R-NH2) provided mono, 1,3-disubstituted symmetrical and unsymmetrical thioureas, which on desulfurization with molecular iodine (I2) led to formation of the corresponding heterocumulene (cyanamides or carbodiimides). The in situ generated heterocumulene on subsequent treatment with sodium azide at room temperature gave corresponding tetrazoles. The product regioselectivity for unsymmetrical 1,3-disubstituted thioureas was found to be correlated with the basicities (pKa's) of the parent amines attached to the thiourea. Aryl-sec-alkyl unsymmetrical thioureas gave thioamido guanidino products rather than the 5-aminotetrazoles produced by HgCl2 mediation of the reaction. Bis-thioureas derived from aryl isothiocyanates and hydrazine gave thiadiazoles exclusively.
Yella, Ramesh,Khatun, Nilufa,Rout, Saroj Kumar,Patel, Bhisma K.
experimental part
p. 3235 - 3245
(2011/06/20)

Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 1
Structure-activity relationships of three related series of 4-phenylthiazol-5-ylacetic acids, derived from two hits emanating from a focused library obtained by in silico screening, have been explored as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Several compounds with double digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained in all subclasses. The most potent compound was [2-(4-chloro-benzyl)-4-(4-phenoxy-phenyl)-thiazol-5-yl]acetic acid having an binding affinity of 3.7 nM and functional antagonistic effect of 66 nM in a BRET and 12 nM in a cAMP assay with no functional activity for the other PGD2 DP receptor (27 μM in cAMP).
Rist, ystein,Grimstrup, Marie,Receveur, Jean-Marie,Frimurer, Thomas M.,Ulven, Trond,Kostenis, Evi,Hoegberg, Thomas
scheme or table
p. 1177 - 1180
(2010/06/15)

Microwave-assisted synthesis of benzothiazoleurea derivatives
A simple and efficient method has been developed for the synthesis of 1-substituted-3-(4-chlorobenzo[d]thiazol-2-yl) ureas (5), from substituted aromatic or aliphatic amino compounds and phenyl 4-chlorobenzo[d]thiazol-2-yl carbamate 4 using microwave irradiation without phosgene in good yields. The title products were characterised by 1H NMR, ESI-MS, and elemental analysis.
Chen, Wenbin,Li, Kejian,Wang, Yong,Xi, Zhen
experimental part
p. 75 - 79
(2010/06/16)

4-Pyridylanilinothiazoles that selectively target von Hippel - Lindau deficient renal cell carcinoma cells by inducing autophagic cell death
Renal cell carcinomas (RCC) are refractory to standard therapy with advanced RCC having a poor prognosis; consequently treatment of advanced RCC represents an unmet clinical need. The von Hippel-Lindau (VHL) tumor suppressor gene is mutated or inactivated in a majority of RCCs. We recently identified a 4-pyridyl-2-anilinothiazole (PAT) with selective cytotoxicity against VHL-deficient renal cells mediated by induction of autophagy and increased acidification of autolysosomes. We report exploration of structure-activity relationships (SAR) around this PAT lead. Analogues with substituents on each of the three rings, and various linkers between rings, were synthesized and tested in vitro using paired RCC4 cell lines. A contour map describing the relative spatial contributions of different chemical features to potency illustrates a region, adjacent to the pyridyl ring, with potential for further development. Examples probing this domain validated this approach and may provide the opportunity to develop this novel chemotype as a targeted approach to the treatment of RCC. 2009 American Chemical Society.
Hay, Michael P.,Turcotte, Sandra,Flanagan, Jack U.,Bonnet, Muriel,Chan, Denise A.,Sutphin, Patrick D.,Nguyen, Phuong,Giaccia, Amato J.,Denny, William A.
supporting information; experimental part
p. 787 - 797
(2010/07/05)

Microwave induced improved synthesis of monoaryl thiocarbamides, 1,3-diarylthiocarbamides, 1,3-diarylcarbamides and monoaryl-2,4-dithiobiurets
The 1-arylthiocarbamides (3), 1, 3-diarylthiocarbamides (6), 1,3-diarylcarbamides (7) and 1-aryl-2,4-dithiobiurets (11) have been synthesized by the microwave induced heating of respective reactants for about 30-60 s in solvent free condition. Reaction yields are higher with reduced time, period and without the use of any solvent.
Uberhande,Thakare,Berad
experimental part
p. 1137 - 1141
(2011/05/05)

Synthesis and anticonvulsant activity of halo-substituted aryl urea and thioureas
Halo-substituted arylureas have been prepared by condensation of halo-substituted primary arylamine with sodium cyanate and halo-substituted arylthioureas have been prepared by condensation of halo-substituted primary arylamine with ammonium thiocyanate in presence of acid. The structures of compounds synthesized have been confirmed by elemental analysis and spectral data. Their anticonvulsant activity was evaluated, p-bromophenyl urea and p-chlorophenyl and p-bromophenyl thioureas were found to be most active in the maximal electro shock (MES) test. p-Bromophenyl derivatives were found least neurotoxic in the rotorod test. The results were compared with standard drug phenytoin.
Gupta, Mahesh Kumar,Pandeya, Suerendra N.,Zaiad, Golal M.,Gangwar
experimental part
p. 1421 - 1424
(2011/09/20)

An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine(III) reagent
In a one-pot strategy we have achieved an efficient method for the synthesis of organic cyanamides starting from dithiocarbamic acid salts/amines. In this strategy the in situ generated alkyl or aryl isothiocyanates, obtained by the desulfurization of dithiocarbamic acid salts with diacetoxyiodobenzene (DIB) react with aqueous ammonia forming alkyl or aryl thiourea which on subsequent oxidative desulfurization with DIB led to the formation of corresponding cyanamide in good yields. Mild reaction conditions, shorter reaction time, an environmentally benign protocol, and easy isolation of the desired product make the present methodology a suitable alternative for the preparation of various organic cyanamides.
Ghosh, Harisadhan,Yella, Ramesh,Ali, Abdur Rezzak,Sahoo, Santosh K.,Patel, Bhisma K.
experimental part
p. 2407 - 2410
(2009/07/26)

HETEROARYL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE IN CANCER TREATMENT
Provided herein are novel heteroaryl compounds, compositions comprising the compounds, and methods of treatment or prevention comprising administration of the compounds. The compounds are effective in the targeting of cells defective in the von Hippel-Lindau gene and in inducing autophagic cell death. The methods are directed to treating or preventing diseases such as cancer, and in particular cancers resulting from von Hippel-Lindau disease. The compounds of the invention may be administered in combination with another therapeutic agent.
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Page/Page column 141

(2009/10/22)

A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
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.
Nath, Jayashree,Patel, Bhisma K.,Jamir, Latonglila,Sinha, Upasana Bora,Satyanarayana
experimental part
p. 1503 - 1506
(2010/05/18)

Design, synthesis, cytoselective toxicity, structure-activity relationships, and pharmacophore of thiazolidinone derivatives targeting drug-resistant lung cancer cells
Ten cytoselective compounds have been identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM. Structure-activity relationship studies revealed that (1) the nitrogen atom on the 4-thiazolidinone ring (ring B in Figure 1) cannot be substituted, (2) several substitutions on ring A are tolerated at various positions, and (3) the substitution on ring C is restricted to the -NMe2 group at the 4-position. A pharmacophore derived from active molecules suggested that two hydrogen bond acceptors and three hydrophobic regions were common features. Activities against P-gp-overexpressing and paclitaxel-resistant cell line H460taxR and modeling using a previously validated P-gp substrate pharmacophore suggested that active compounds were not likely P-gp substrates.
Zhou, Hongyu,Wu, Shuhong,Zhai, Shumei,Liu, Aifeng,Sun, Ying,Li, Rongshi,Zhang, Ying,Ekins, Sean,Swaan, Peter W.,Fang, Bingliang,Zhang, Bin,Yan, Bing
p. 1242 - 1251
(2008/12/23)

Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists
A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC50 values of the most potent antagonists were ca. 0.050 μM in these assays.
Xi, Ning,Bo, Yunxin,Doherty, Elizabeth M.,Fotsch, Christopher,Gavva, Narender R.,Han, Nianhe,Hungate, Randall W.,Klionsky, Lana,Liu, Qingyian,Tamir, Rami,Xu, Shimin,Treanor, James J.S.,Norman, Mark H.
p. 5211 - 5217
(2007/10/03)

A convenient and efficient method for the synthesis of mono- and N,N-disubstituted thioureas
A convenient method for the synthesis of mono- and N,N-disubstituted thioureas by the debenzoylation of N-substituted- and N,N-disubstituted- N′-benzoylthioureas with hydrazine hydrate under solvent-free conditions has been developed. N-Substituted-N′-benzoylthioureas and hydrazine hydrate were mixed, and stirred at room temperature without a solvent to give the corresponding N-substituted thioureas in high yields.
Kodomari, Mitsuo,Suzuki, Masato,Tanigawa, Keiko,Aoyama, Tadashi
p. 5841 - 5843
(2007/10/03)

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors
The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.
Wilson, Kenneth J.,Illig, Carl R.,Subasinghe, Nalin,Hoffman, James B.,Jonathan Rudolph,Soll, Richard,Molloy, Christopher J.,Bone, Roger,Green, David,Randall, Troy,Zhang, Marie,Lewandowski, Frank A.,Zhou, Zhao,Sharp, Celia,Maguire, Diane,Grasberger, Bruce,DesJarlais, Renee L.,Spurlino, John
p. 915 - 918
(2007/10/03)

Substituted N-phenylisothioureas: Potent inhibitors of human nitric oxide synthase with neuronal isoform selectivity
S-Ethyl N-phenylisothiourea (4) has been found to be a potent inhibitor of both the human constitutive and inducible isoforms of nitric oxide synthase. A series of substituted N-phenylisothiourea analogues was synthesized to investigate the structure-activity relationship of this class of inhibitor. Each analogue was evaluated for human isoform selectivity. One analogue, S-ethyl N-[4-(trifluoromethyl)phenyl]isothiourea (39), exhibited 115-fold and 29-fold selectivity for the neuronal isoform versus the inducible and endothelial derived constitutive isoforms, respectively. Studies have shown the substituted N-phenylisothiourea 39 binds competitively with L,-arginine.
Shearer, Barry G.,Lee, Shuliang,Oplinger, Jeffrey A.,Frick, Lloyd W.,Garvey, Edward P.,Furfine, Eric S.
p. 1901 - 1905
(2007/10/03)

New antiarrhythmic agents. Piperazine guanidine derivatives
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Pascal,Pinhas,Laure,Dumez,Poizot
p. 81 - 85
(2007/10/02)

Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas
An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N'-benzoylthioureas with 5percent aqueous sodium hydroxide.Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g. 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.
Rasmussen, C. R.,Villani, F. J.,Weaner, L. E.,Reynolds, B. E.,Hood, A. R.,et al.
p. 456 - 459
(2007/10/02)

Synthesis and Characterization of Coordination Polymers of Cobalt(II) and Nickel(II) with Some Monoarylthioureas
The coordination polymers of cobalt(II) and nickel(II) with N-phenyl-, o-chlorophenyl- and p-chlorophenyl-thioureas have been synthesised.The elemental analyses show the composition of the complexes as n, n, and n.The IR spectral studies show that coordination occurs through sulphur and nitrogen atoms of the ligands.The electronic spectral and magnetic measurements studies reveal octahedral geometry around the metal ions.On the basis of insolubility of complexes, and their high thermal stabilities, polymeric structures are proposed for these complexes.
Bajpai, Anjali,Mishra, D. D.,Bajpai, U. D. N.
p. 1072 - 1074
(2007/10/02)

Heterocyclic derivatives of guanidine
5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.
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(2008/06/13)

Synthesis & Pharmacological Evaluation of Ethyl 3-Substituted-phenyl-2-methylmercapto/ phenyl/ methyl-4(3H)-pyrimidone-5-carboxylates
A number of ethyl 3-substituted-phenyl-2-methylmercapto/ phenyl/ methyl-4(3H)-pyrimidone-5-carboxylates (V) have been prepared by the reaction of amidines (III) with diethyl ethoxymethylenemalonate.In order to confirm the structure (V), ethyl 3-(2'-methylphenyl)-2-methylmercapto-4(3H)pyrimidone-5-carboxylate (103) has been transformed into the earlier synthesised 3-(2'-methylphenyl)-2-methylmercapto-4(3H)-pyrimidone (115) by decarboxylation of 3-(2'-methylphenyl)-2-methylmercapto-4(3H)-pyrimidone-5-carboxylic acid (114), obtained by the alkaline hydrolysis of 103.Someof these compounds have shown antiinflammatory, diuretic and antipassive cutaneous anaphylaxis activities.
Gupta, K. A.,Saxena, Anil K.,Jain, Padam C.
p. 228 - 233
(2007/10/02)

Studies on phenothiazines. VII. (1). Synthesis of 3-substituted 2-aminobenzenethiols and their conversion into phenothiazines
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Gupta,Ojha,Kumar
p. 1325 - 1327
(2007/10/02)

A CONVENIENT AND SINGLE STEP SYNTHESIS OF SUBSTITUTED 4H-BENZOTHIAZINES.
A simple one step synthesis is reported for substituted 4H-benzothiazines involving the condensation of 5-(chloro, bromo, methyl, methoxy, ethoxy)-, 4-methyl- and 3-(chloro and methoxy)-2-aminobenzenethiols with acetylacetone/ethyl acetoacetate/dibenzoylmethane in DMSO.
Gupta, R. R.,Ojha, K. G.,Kalwania, G. S.,Kumar, M.
p. 1145 - 1149
(2007/10/02)