- Aqueous microwave-assisted one-pot synthesis of N-substituted rhodanines
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Two aqueous, one-pot, microwave-assisted methods for the rapid synthesis of N-substituted rhodanines from amine substrates are described. Alkyl- and benzylamines could be converted into the corresponding rhodanines with an atom-efficient one-pot, three-step protocol based on carbon disulfide and chloroacetic acid in short reaction times and good to excellent yields. An alternative, microwave-assisted one-pot, one-step protocol using bis(carboxymethyl)trithiocarbonate in water was developed for the synthesis of N-arylrhodanines from anilines.
- Nitsche, Christoph,Klein, Christian D.
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Read Online
- A facile one-pot, four-component synthesis of (Z)-isomer of rhodanine-oxindole derivatives under environmentally benevolent conditions
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Herein, an efficient and sustainable one-pot, four-component access to rhodanine-oxindole derivatives is achieved by a reaction between primary amines, carbon disulfide, ethyl chloroacetate, and cyano-substituted alkenyl oxindoles. The reaction was conducted without any harsh conditions as well as exhausting workup in polyethylene glycol (PEG) as a green solvent at room temperature and delivered rhodanine-oxindole products in high yield. This publication is the first easy protocol to be reported for the rapid construction of new rhodanine-oxindole derivatives at room temperature without harsh conditions and via multicomponent reaction.
- Aghamiri, Bagher,Jalalinik, Mahbod,Moghaddam, F. Matloubi
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supporting information
(2021/12/31)
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- HETEROCYCLIC INTEGRIN AGONISTS
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The present invention provides polycyclic oxothioxoimidazolidines, dioxoimidazolines, oxothioxooxazolidines, dioxooxazolidines, and related compounds, which are useful as integrin agonists. Methods for the treatment of integrin-mediated diseases such as cancer are also described.
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Paragraph 0285; 0286
(2018/07/29)
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- IDO inhibitors
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Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.
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Page/Page column 297; 298; 299
(2018/09/02)
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- Novel rhodanines with anticancer activity: Design, synthesis and CoMSIA study
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Three different series of some novel N-substituted rhodanines were designed for anticancer activity and prepared from the corresponding dithiocarbamates. The synthesized compounds were analyzed by IR, NMR and MASS to confirm their structures. All the titl
- Mandal, Subhankar P.,Mithuna,Garg, Aakriti,Sahetya, Sanjana S.,Nagendra,Sripad,Manjunath, Mendon Manisha,Sitaram,Soni, Mukesh,Baig, R. Nasir,Kumar, S. Vasanth,Kumar, B. R. Prashantha
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p. 58641 - 58653
(2016/07/06)
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- Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture
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The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.
- Nitsche, Christoph,Schreier, Verena N.,Behnam, Mira A. M.,Kumar, Anil,Bartenschlager, Ralf,Klein, Christian D.
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p. 8389 - 8403
(2013/12/04)
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- Small molecule fusion inhibitors: Design, synthesis and biological evaluation of (Z)-3-(5-(3-benzyl-4-oxo-2-thioxothiazolidinylidene)methyl)-N-(3- carboxy-4-hydroxy)phenyl-2,5-dimethylpyrroles and related derivatives targeting HIV-1 gp41
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By a scaffold elongation strategy, a series of (Z)-3-(5-(3-benzyl-4-oxo-2- thioxothiazolidinylidene)methyl)-N-(3-carboxy-4-hydroxy)phenyl-2, 5-dimethylpyrroles and related derivatives with a linear multi-aromatic-ring skeleton were designed, synthesized, and evaluated in HIV-1 gp41 and cellular assays. Among them, the most active compounds, 12e, 12g, and 12k with a one-carbon linker (n = 1) between the rhodanine (C) and phenyl (D) rings, exhibited very promising inhibitory potency with IC50 values of 1.8-2.6 μM and EC50 values of 0.3-1.5 μM against gp41 6-HB formation and HIV-1 replication in MT-2 cells, respectively. Additionally, they were almost equally effective against both T20-sensitive and resistant strains. The related SAR studies and molecular modeling results provided potential for further developing a new class of non-peptide small molecular fusion inhibitors targeting the HIV-1 gp41.
- He, Xiao-Yang,Lu, Lu,Qiu, Jiayin,Zou, Peng,Yu, Fei,Jiang, Xing-Kai,Li, Lin,Jiang, Shibo,Liu, Shuwen,Xie, Lan
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p. 7539 - 7548
(2013/11/19)
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- Design, synthesis and biological evaluation of 3-substituted 2,5-dimethyl-N-(3-(1H-tetrazol-5-yl)phenyl)pyrroles as novel potential HIV-1 gp41 inhibitors
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Based on the structure of HIV-1 gp41 binding site for small-molecule inhibitors, optimization of lead 2 resulted in the discovery of a new series of 2,5-dimethyl-3-(5-(N-phenylrhodaninyl)methylene)-N-(3-(1H-tetrazol-5-yl)phenyl) pyrrole compounds with improved anti-HIV-1 activity. The most active compounds 13a and 13j exhibited significant potency against gp41 6-HB formation with IC50 values of 4.4 and 4.6 μM and against HIV-1 replication in the MT-2 cells with EC50 values of 3.2 and 2.2 μM, respectively, thus providing a new starting point to develop highly potent small-molecule HIV fusion inhibitors targeting gp41.
- He, Xiao-Yang,Zou, Peng,Qiu, Jiayin,Hou, Ling,Jiang, Shibo,Liu, Shuwen,Xie, Lan
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experimental part
p. 6726 - 6734
(2011/12/04)
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- A Versatile and Practical Synthesis toward the Development of Novel HIV-1 Integrase Inhibitors
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As a continuation of our previous work, which resulted in the identification of a new hit compound as an HIV-1 integrase inhibitor, three novel series of salicylic acid derivatives were synthesized using three versatile and practical synthetic strategies and were assayed for their capacity to inhibit the catalytic activity of HIV-1 integrase. Biological evaluations revealed that some of the synthesized compounds possess good inhibitory potency in enzymatic assays and are able to inhibit viral replication in MT-4 cells at low micromolar concentrations. Finally, docking studies were conducted to analyze the binding mode of the synthesized compounds within the DNA binding site of integrase in order to refine their structure-activity relationships. Easy as A, B, C: Three new series of salicylic acid derivatives were designed and synthesized to investigate their activity toward HIV-1 integrase. Some of these compounds were obtained with microwave-assisted procedures developed and optimized in our research group, which allowed us to rapidly generate several final compounds of high purity.
- Rinaldi, Marta,Tintori, Cristina,Franchi, Luigi,Vignaroli, Giulia,Innitzer, Anna,Massa, Silvio,Este, Jose A.,Gonzalo, Encarna,Christ, Frauke,Debyser, Zeger,Botta, Maurizio
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experimental part
p. 343 - 352
(2012/01/11)
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- Electrogenerated base-promoted synthesis of N-benzylic rhodanine and carbamodithioate derivatives
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Electrogenerated magnesium-associated cyanomethyl anions/bases obtained from the electrochemical reduction of acetonitrile and the oxidation of a sacrificial magnesium rod were successfully used to promote the addition of carbon disulfide to primary benzylic amines. Alkylation with ethyl 3-bromopropionate acid ester or with ethyl 2-bromoacetate acid ester yields the corresponding ring-opened carbamodithioate compounds or cyclic rhodanine derivatives, respectively. The effect of the amount of electrogenerated base on the yield of reaction was also evaluated.
- Tissaoui, Khalil,Raouafi, Noureddine,Boujlel, Khaled
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experimental part
p. 41 - 48
(2010/10/03)
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- Practical one-pot two-step protocol for the microwave-assisted synthesis of highly functionalized rhodanine derivatives
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A fast and efficient protocol for the generation of substituted 5-arylidene rhodanines in a sequential one-pot two-step process combining the "Holmberg method" and the Knoevenagel condensation under microwaveassisted conditions has been developed. The final compounds 11a-k have been obtained in high yield and purity after a simple precipitation from, methanol, making this procedure facile, practical, and rapid to execute.
- Radi, Marco,Botta, Lorenzo,Casaluce, Gianni,Bernardini, Martina,Botta, Maurizio
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experimental part
p. 200 - 205
(2010/10/19)
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- USE OF THIAZOLIDINONE DERIVATIVES AS ANTIANGIOGENIC AGENTS
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The invention relates to the use of compounds of general formula (I), in which R1, R2 and X are as defined in the description for the preparation of pharmaceutical compositions for the treatment of pathologies in which inhibition of the interaction between HIF-1α and p300 is beneficial, in particular as antiangiogenic medicaments for the therapy of solid tumors.
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Page/Page column 13
(2008/06/13)
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- SAR and 3D-QSAR studies on thiadiazolidinone derivatives: Exploration of structural requirements for glycogen synthase kinase 3 inhibitors
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The 2,4-disubstituted thiadiazolidinones (TDZD) are described as the first ATP-noncompetitive GSK-3 inhibitors. Following an SAR study about TDZD, different structural modifications in the heterocyclic ring aimed to test the influence of each heteroatom o
- Martinez, Ana,Alonso, Mercedes,Castro, Ana,Dorronsoro, Isabel,Gelpí, J. Luis,Luque, F. Javier,Pérez, Conceptión,Moreno, Francisco J.
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p. 7103 - 7112
(2007/10/03)
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- Traceless solid-phase synthesis of 2-amino-5-alkylidene-thiazol-4-ones
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2-Amino-5-alkylidene-thiazol-4-ones bearing two diversity points are prepared by a solid-phase strategy exploiting rhodanine as the starting material. Rhodanine is first loaded on bromo-Wang resin, subjected to Knovenagel condensation with aldehydes, and cleaved off the resin in a traceless manner by means of an amine.
- Pulici, Maurizio,Quartieri, Francesca
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p. 2387 - 2391
(2007/10/03)
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- RHODANINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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This invention describes rhodanine derivatives and pharmaceutical compositions useful as inhibitors of ubiquitination. The compounds and compositions of the invention are useful as inhibitors of the biochemical pathways of organisms in which ubiquitinatio
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- Phospholipase D inhibitors and uses thereof
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The invention is directed to thiazolidinones and the use thereof to inhibit phospholipase D (PLD) activity. The invention further relates to methods of treating cancer and inflammatory diseases using thiazolidinones.
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- Enzyme inhibitors
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Compounds of general formula (I): where A, E, G, X, Y and the bond - - - take various meanings are of use in the preparation of a pharmaceutical formulation, for example in the treatment of a disease in which GSK-3 is involved, including Alzheimer's disea
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Page/Page column 12
(2010/01/31)
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- Arylalkylidene rhodanine with bulky and hydrophobic functional group as selective HCV NS3 protease inhibitor
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Arylalkylidene rhodanines 2(a-d) inhibit HCV NS3 protease at moderate concentrations. They are better inhibitors of other serine proteases such as chymotrypsin and plasmin. However, the selectivity of arylmethylidene rhodanines (8a, 9a) with bulkier and more hydrophobic functional groups increases by 13- and 25-fold towards HCV NS3 protease respectively.
- Sing, Wan Theng,Lee, Cheng Leng,Yeo, Su Ling,Lim, Siew Pheng,Sim, Mui Mui
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