- A New Synthesis Strategy for Rhodanine and Its Derivatives
-
Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N -aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid, which provides a new approach of the synthesis of rhodanine and its derivatives. The developed strategy is straightforward, efficient, atom economical, and convenient in good yields.
- Pan, Zhenliang,An, Wankai,Wu, Lulu,Fan, Liangxin,Yang, Guoyu,Xu, Cuilian
-
p. 1131 - 1134
(2021/05/25)
-
- Design, synthesis and biological evaluation of imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as lymphoid-specific tyrosine phosphatase inhibitors
-
Lymphoid-specific tyrosine phosphatase (LYP), which exclusively exists in immune cells and down-regulates T cell receptor signaling (TCR), has becoming a potent target for various autoimmune diseases. Herein, we designed and synthesized imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as new LYP inhibitors. Among them, the cinnamic acids-based inhibitors (9p and 9r) displayed good LYP inhibitory activities (IC50 = 2.85–6.95 μM). Especially, the most potent inhibitor 9r was identified as competitive inhibitor (Ki = 1.09 μM) and bind LYP reversibly. Meanwhile, 9r exhibited better selectivity over other phosphatases than known LYP inhibitor A15. Furthermore, compound 9r could regulate TCR associated signaling pathway in Jurkat T cell.
- Liang, Xiao,Fu, Huansheng,Xiao, Peng,Fang, Hao,Hou, Xuben
-
-
- Synthesis and Biological Evaluation of Novel Carbazole Hybrids as Promising Antimicrobial Agents
-
Two series of carbazole analogs of 8-methoxy-N-substituted-9H-carbazole-3-carboxamides (series 1) and carbazolyl substituted rhodanines (series 2) were synthesized through facile synthetic routes. All the final compounds from these two series were evaluated for their preliminary in vitro antifungal and antibacterial activity against four fungal (Candida albicans, Cryptococcus neoformans, Cryptococcus tropicalis and Aspergillus niger) and four bacterial (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) strains, respectively. Among the tested compounds, three compounds of series 1 displayed promising antifungal and antibacterial activity, especially against C. neoformans and S. aureus. In addition, one compound of series 1 displayed notable antimicrobial activity (MIC: 6.25 μg/mL) against clinical isolates of C. albicans and C. neoformans (MIC: 12.5 μg/mL). From the second series, four compounds exhibited significant antifungal and antibacterial activity, especially against C. neoformans and S. aureus. The most active compound of series 2 displayed a prominent antimicrobial activity against C. neoformans (MIC: 3.125 μg/mL) and S. aureus (MIC: 1.56 μg/mL), respectively.
- Shaikh, Mahamadhanif S.,Chandrasekaran, Balakumar,Palkar, Mahesh B.,Kanhed, Ashish M.,Kajee, Afsana,Mlisana, Koleka P.,Singh, Parvesh,Ghai, Meenu,Cleopus Mahlalela, Mavela,Karpoormath, Rajshekhar
-
-
- Compound with piperine skeleton structure as well as preparation and application thereof
-
The invention discloses a compound with a piperine skeleton structure as well as preparation and application of the compound, wherein the structural formulas of the compound are shown as a formula I-1and a formula I-2; in the formulas, R1 is hydrogen, halogen, nitryl or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, C1-C5 straight-chain or branched-chain alkyl and C1-C5 alkoxy; R2 is hydrogen, halogen, nitro or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, phenyl, aryl and aromatic heterocyclic group, or substituted or unsubstituted C1-C5 straight-chain or branched-chain alkyl, or substituted or unsubstituted C1-C5 alkoxy, or substituted or unsubstituted C6-C30 aryl, fused ring and fused heterocyclic ring. As a chitinase inhibitor, the compound provided by the invention has the advantages of high activity, good broad spectrum and easiness in synthesis, and shows excellent insecticidal ability and insecticidal spectrum.
- -
-
Paragraph 0044; 0051-0053
(2020/07/02)
-
- Synthesis, characterization, antibacterial and antioxidant potency of nsubstituted- 2-sulfanylidene-1,3-thiazolidin-4-one derivatives and QSAR study
-
Background: Rhodanine is known for its potential and important role in the medicinal chemistry since its derivatives exhibit a wide range of pharmacological activities such as antibacterial, antifungal, antidiabetic, antitubercular, anti-HIV, antiparasitic, antioxidant, anticancer, antiproliferative and anthelmintic agents. Objectives: Since N-substituted rhodanine synthons are rarely commercially available, it is desirable to develop a straightforward synthetic approach for the synthesis of these key building blocks. The objective was to synthesize a series of rhodanine derivatives and to investigate their antimicrobial and antioxidant activity. Also, in order to obtain an insight into their structure-activity relationship, QSAR studies on the antioxidant activity were performed. Methods: 1H and 13C FTNMR spectra were recorded on Bruker Avance 600 MHz NMR Spectrometer, mass analysis was carried out on ESI+ mode by LC-MS/MS API 2000. 2,2-Diphenyl-1- picrylhydrazyl radical scavenging activity (% DPPH) was determined in dimethylsulfoxide (DMSO) as a solvent. The antibacterial activity was assessed against Bacillus subtilis, Staphylococcus aureus (Gram positive) and Escherichia coli, Pseudomonas aeruginosa (Gram negative) bacteria in terms of the minimum inhibitory concentrations (MICs) by a modified broth microdilution method. Results: A series of N-substituted-2-sulfanylidene-1,3-thiazolidin-4-ones were synthesized and characterized by 1H NMR, 13C NMR, FTIR, GC MS, LCMS/MS and C,H,N,S elemental analysis. Most of the synthesized compounds showed moderate to excellent antibacterial activity (MIC values from 125 μg/ml to 15.62 μg/mL) and DPPH scavenging activity (from 3.60% to 94.40%). Compound 2-thioxo-3- (4-(trifluoromethyl)-phenyl)thiazolidin-4-one showed the most potent activity against Escherichia coli (3.125 μg/mL), equivalent to antibiotic Amikacin sulphate and against Staphylococcus aureus (0.097 μg/ml), 100 times superior then antibiotic Amikacin sulphate. It has also shown a potent antioxidant activity (95% DPPH scavenging). Two best QSAR models, obtained by GETAWAY descriptor R7p+, Balabans molecular connectivity topological index and Narumi harmonic topological index (HNar), suggest that the enhanced antioxidant activity is related to the presence of pairs of atoms higher polarizability at the topological distance 7, substituted benzene ring and longer saturated aliphatic chain in N-substituents. Conclusion: A series of novel N-substituted-2-thioxothiazolidin-4-one derivatives were designed, synthesized, characterized and evaluated for their antibacterial and antioxidant activity in vitro. Majority of the compounds showed excellent antibacterial activity compared to ampicillin and few of them have an excellent activity as compared to Chloramphenicol standard antibacterial drug. The QSAR study has clarified the importance of presenting a pairs of atoms higher polarizability, such as Cl and S at the specific distance, as well as the substituted benzene ring and a long saturated aliphatic chain in N-substituents for the enhanced antioxidant activity of 2-sulfanylidene-1,3- thiazolidin-4-one derivatives.
- Brahmbhatt, Harshad,Molnar, Maja,Pavi?, Valentina,Rastija, Vesna
-
p. 840 - 849
(2020/01/25)
-
- Synthesis of 5-substituted 2-ylidene-1,3-thiazolidin-4-one derivatives and evaluation of their anticancer and antioxidant activities
-
[Figure not available: see fulltext.] Novel 5-(aroyl)methyl- and 5-(aroyl)methylen-2-ylidene-1,3-thiazolidin-4-ones have been prepared in high yields using ketene N,S-acetal salts, obtained from phenyl isothiocyanate and propanedinitrile or ethyl cyanoacetate. Several of the newly synthesized 1,3-thiazolidin-4-one derivatives demonstrate high antioxidant and anticancer activities.
- Saied, Khaled F.,Kandeel, Kamal A.,Abdelwahab, Salwa S.,Ahmed, Osama M.
-
p. 993 - 1003
(2019/11/16)
-
- Discovery of novel N-methyl carbazole tethered rhodanine derivatives as direct inhibitors of Mycobacterium tuberculosis InhA
-
InhA (Enoyl-ACP reductase) plays a crucial role in the biosynthetic pathway of cell wall synthesis in Mycobacterium tuberculosis (Mtb). Isoniazid (INH) is an important first-line drug, which inhibits InhA. The rapid increase in resistance to INH and currently marketed drugs as well as emergence of MDR-TB and XDR-TB has complicated the diagnosis and treatment of Mtb with ever increasing threat to human kind. Herein, we report novel N-methyl carbazole derivatives as potential anti-TB compounds acting directly via InhA inhibition. All the synthesized final compounds were screened against Mtb virulent cell line H37Rv and investigated the InhA enzyme inhibition. Interestingly, compound 9e displayed promising inhibition (91%) at 50 μM concentration and IC50 of 2.82 μM against InhA. To understand the ligand receptor interaction between compound 9e and InhA, molecular docking and molecular dynamics experiments were performed. The computational results were in agreement with the observed experimental data. Further, the cytotoxicity studies on mammalian cells revealed that all the compounds were safe.
- Shaikh, Mahamadhanif S.,Kanhed, Ashish M.,Chandrasekaran, Balakumar,Palkar, Mahesh B.,Agrawal, Nikhil,Lherbet, Christian,Hampannavar, Girish A.,Karpoormath, Rajshekhar
-
supporting information
p. 2338 - 2344
(2019/06/20)
-
- Unexpected Synthesis of 2,3,5,6-Tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by a Double Michael Addition/CS2 Extrusion/Double Cyclization Sequence
-
Bis adducts derived from a double Michael addition of rhodanine to an azo-ene system of two molecules of 1,2-diaza-1,3-dienes (DDs) have furnished the corresponding 2,3,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by means of a CS2 extrusion/double cyclization sequence. The incorporation of two units (4 and 2 atoms) of DDs into the fused bicyclic heterocycles represents a new application of this versatile class of molecules in heterocyclic synthesis.
- Mari, Giacomo,De Crescentini, Lucia,Favi, Gianfranco,Santeusanio, Stefania,Lillini, Samuele,Mantellini, Fabio
-
p. 6291 - 6298
(2017/11/21)
-
- 3. 5 - disubstituted the rhodanine class anti-withers apoptotic protein Bcl - 2 inhibitor and preparation method and application
-
The invention discloses a 3,5-disubstituted rhodanine anti-apoptosis protein Bc1-2 inhibitor as well as preparation method and an application thereof. The compound has a structure of a general formula I. The compound disclosed by the invention has high inhibitory activity on Bc1-2 and can be used for preparation of medicines for preventing or treating related mammal diseases caused by abnormal expression of anti-apoptosis protein Bc1-2. The invention also relates to a pharmaceutical application of a composition of the compound with the structure of the general formula I. The structural formula is as shown in the specification.
- -
-
Paragraph 0106-0107
(2017/08/25)
-
- Synthesis and biological evaluation of new rhodanine analogues bearing 2-chloroquinoline and benzo[h]quinoline scaffolds as anticancer agents
-
Several rhodanine derivatives (9-39) were synthesized for evaluation of their potential as anticancer agents. Villsmeier cyclization to synthesize aza-aromatic aldehydes, rhodanine derivatives preparation and Knoevenagel type of condensation between the rhodanines and aza-aromatic aldehydes are key steps used for the synthesis of 31 compounds. In vitro antiproliferative activity of the synthesized rhodanine derivatives (9-39) was studied on a panel of six human tumor cell lines viz. HGC, MNK-74, MCF-7, MDAMB-231, DU-145 and PC-3 cell lines. Some of the compounds were capable of inhibiting the proliferation of cancer cell lines at a micromolar concentration. Six compounds are found to be potent against HGC cell lines; compound 15 is found to be active against HGC - Gastric, MCF7 - Breast Cancer and DU145 - Prostate Cancer cell lines; compound 39 is potent against MNK-74; four compounds are found to be potent against MCF-7 cell lines; three compounds are active against MDAMB-231; nine compounds are found to be potent against DU-145; three compounds are active against PC-3 cell lines. These compounds constitute a promising starting point for the development of novel and more potent anticancer agents in future.
- Ramesh, Vadla,Ananda Rao, Boddu,Sharma, Pankaj,Swarna,Thummuri, Dinesh,Srinivas, Kolupula,Naidu,Jayathirtha Rao, Vaidya
-
p. 569 - 580
(2014/07/21)
-
- Methods of Making and Using Thioxothiazolidine and Rhodanine Derivatives as HIV-1 and JSP-1 Inhibitors
-
The present invention provides methods of making and using 5-(2-(indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one derivatives having HIV-1 or JSP-1 inhibitory activity.
- -
-
Paragraph 0055; 0056
(2013/10/07)
-
- 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
-
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
-
p. 7539 - 7548
(2013/11/19)
-
- Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture
-
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.
-
p. 8389 - 8403
(2013/12/04)
-
- Aqueous microwave-assisted one-pot synthesis of N-substituted rhodanines
-
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.
-
p. 5197 - 5201
(2012/10/30)
-
- An efficient microwave assisted synthesis of novel class of Rhodanine derivatives as potential HIV-1 and JSP-1 inhibitors
-
(Z)-5-(2-(1H-Indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4- one (7a-q) derivatives have been synthesized by the condensation reaction of 3-phenyl-2-thioxothiazolidin-4-ones (3a-h) with suitably substituted 2-(1H-indol-3-yl)-2-oxoacetaldehyde (6a-d) under microwave condition. The thioxothiazolidine-4-ones were prepared from the corresponding aromatic amines (1a-e) and di-(carboxymethyl)-trithiocarbonyl (2). The aldehydes (6a-h) were synthesized from the corresponding acid chlorides (5a-d) using HSnBu 3.
- Kamila, Sukanta,Ankati, Haribabu,Biehl, Edward R.
-
scheme or table
p. 4375 - 4377
(2011/09/19)
-
- 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
-
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
-
experimental part
p. 6726 - 6734
(2011/12/04)
-
- An expeditious, environment-friendly, and microwave-assisted synthesis of 5-isatinylidenerhodanine derivatives
-
A series of nine 5-arylidenerhodanine derivatives was prepared in good yields and purity without the use of a solvent or catalyst under microwave-assisted condensation with some substituted isatins. All 5-arylidenerhodanines were evaluated as possible inhibitors of the CK1α/β, CDK5/p25, and GSK-3α/β kinases. None of them showed substantive inhibitory activity against these kinases when evaluated at the concentration of 10 μM.
- Safer, Abdelmounaim,Rahmouni, Mustapha,Carreaux, Francois,Paquin, Ludovic,Lozach, Olivier,Meijer, Laurent,Bazureau, Jean Pierre
-
body text
p. 332 - 337
(2012/02/14)
-
- Chemoselectivity of the [2+3]-cycloaddition of thiocarbonyl ylides with 5-benzylidene-3-phenylrhodanine
-
Reactions of three different thiocarbonyl S-methylides, generated from thiobenzophenone (2), 2,2,4,4-tetramethyl-3-thioxocyclobutanone (3), and adamantanethione (8), respectively, and diazomethane, with 5-benzylidene-3- phenylrhodanine (12) were carried out. The aromatic thiocarbonyl ylide la adds chemoselectively to the C,C-double bond, but the spirocyclic 1,3-dithiolane 18, i.e. the [2+3]-cycloadduct with the C=S group of 12, was also formed as a minor product. In the cases of the aliphatic thiocarbonyl ylides 6 and 20, the [2+3]-cycloaddition occurred at the exocyclic C,C-double bond exclusively to give the spirocyclic tetrahydrothiophene derivatives 23 and 21, respectively. A smooth acid-catalyzed decomposition of 18 yielded the 2-diphenylmethylidene derivative 19. The formation of product 24, which was obtained in the reaction of the sterically congested ylide 6 with 12, is explained by a 1,4-H-shift in an intermediate zwitterionic adduct. The structures of the tetrahydrothiophenes 17, 21 and 23, as well as that of 24, were established by X-ray crystallography.
- Seyfried,Linden,Mloston,Heimgartner
-
p. 1363 - 1376
(2007/10/03)
-
- Rhodanine derivatives as inhibitors of JSP-1
-
Dual-specificity phosphatases (DSPs) are a subclass within the protein tyrosine phosphatase family (PTPs). A series of rhodanine-based inhibitors was synthesized and shown to be novel, potent, and selective inhibitors against the DSP family member JNK-stimulating phosphatase-1 (JSP-1). Compounds of this class may be useful for the treatment of inflammatory and proliferative disorders.
- Cutshall, Neil S.,O'Day, Christine,Prezhdo, Marina
-
p. 3374 - 3379
(2007/10/03)
-
- Phospholipase D inhibitors and uses thereof
-
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.
- -
-
-
- AN INFRA-RED SPECTROSCOPIC STUDY OF SOME SUBSTITUTED 1,3-THIAZOLIDIN-4-ONES
-
The infra-red spectra of a series of 2,3-diaryl-1,3-thiazolidin-4-ones were measured and the majority of the absorption bands assigned.The value of the carbonyl stretching frequency was related to the availability of the lone pair on the nitrogen atom of the thiazolidinone ring.The effects of S-oxidation of these compounds on their spectra were examined.The spectra of 3-benzyl-2-phenyl-1,3-thiazolidin-4-one, 3-butyl-2-phenyl-1,3-thiazolidin-4-one, 5-methyl-2,3-diphenyl-1,3-thiazolidin-4-one and 3-phenyl-2-thioxo-1,3-thiazolidine-4-one were also investigated.Key words: 1,3-Thiazolidin-4-ones; 1-oxides; 1,1-dioxides; infra-red spectroscopy.
- Woolston, Christopher Richard J.,Lee, John Barry,Swinbourne, Frederick John
-
p. 223 - 236
(2007/10/02)
-
- Condensation Products of 2-Aminobenzothiazoles and 3-Aryl-5-bromorhodanines
-
Condensation of 2-aminobenzothiazole or its derivatives (I) with 3-aryl-5-bromorhodanines (II) results in the formation of 2,2'-hydrazobisbenzothiazoles (V) and 3-arylrhodanines (VI) instead of the expected products 1-phenylthiazoloimidazobenzothiazole-2(1H)thiones (III) or 3-phenylthiazoloimidazobenzothiazole-2(3H)thiones (IV).
- Gakhar, H. K.,Gupta, Shashi Bhushan
-
p. 681 - 682
(2007/10/02)
-
- REACTION OF CHLOROACETYL CHLORIDE WITH THE SALTS OF N-ALKYL(ARYL)DITHIOCARBAMIC ACIDS - A CONVENIENT METHOD FOR THE SYNTHESIS OF 3-SUBSTITUTED RHODANINES
-
Rhodanine and its 3-substituted derivatives are readily obtained in the reaction of monochloroacetyl chloride with the ammonium salts of N-substituted dithiocarbamic acids.A possible reaction mechanism, involving S -> N-acyl migration, is discussed.
- Krus, K.,Masias, A.,Beletskaya, I. P.
-
p. 1824 - 1825
(2007/10/02)
-
- Condensation Products of 2-Aminobenzenethiols & 5-Bromo-3-phenylrhodanine
-
Condensation of 2-aminobenzenethiol or its 5-methyl derivative (I) with 5-bromo-3-phenylrhodanine (II) results in the formation of 2,2'-diaminodiphenyl disulphide or its 5,5'-dimethyl derivative (V) and 3-phenylrhodanine (VI) instead of the expected 2-mercapto-3-phenyl-3H,9aH-thiazolobenzothiazine or its 7-methyl derivative (IV).
- Gakhar, H. K.,Prabha, Usha,Gill, J. K.
-
p. 469 - 470
(2007/10/02)
-
- 1H and 13C NMR Studies on 3-Aryl-2-thioxo-4-oxazolidinones and 3-Arylrhodanines
-
3-Aryl-2-thioxo-4-oxazolidinones and 3-arylrhodanines have been studied for magnetic non-equivalence of diastereotopically related proton and 13C nuclei in rotational isomers, and for steric interactions between the aryl and heterocyclic moieties of these compounds.For the majority of rotational isomers the barriers to internal rotation about the aryl C-N bond were >100 kJ mol-1, due to the steric bulk of the thiocarbonyl group.Chemical isolation of several of the diastereomers was achieved.The enhanced steric effect and the difference in the electronic effect of the sulphur atom in relation to the oxygen atom appeared to have no influence on the small chemical shift differences of the rotational isomers, detected for some 1H and some 13C nuclei.
- Aksac, Zihni,Pinar, Esat,Icli, Siddik
-
p. 548 - 551
(2007/10/02)
-
- 1,3-Thiazin-4-one
-
Novel cyclized ω-carboxyethyl mono- or dithiocarbanilic acids are disclosed as immunoregulatory agents, useful in the treatment of organ transplant reject phenomenon and autoimmune diseases particularly where a delayed hypersensitivity component has been established, such as multiple sclerosis. Additionally described is the use of certain cyclized ω-carboxyalkyl mono- or dithiocarbamic acids and certain cyclized ω-carboxyalkyl mono- or dithiocarbamic acids.
- -
-
-