cas 513-74-6, Ammonium dithiocarbamate | Articles data

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Synthesis, cytotoxic evaluation and molecular docking study of 2-alkylthio-4-(2,3,4-trimethoxyphenyl)-5-aryl-thiazoles as tubulin polymerization inhibitors
A series of cis-restricted 2-alkylthio-4-(2,3,4-trimethoxyphenyl)-5-aryl- thiazole analogues of combretastatin A-4 were synthesized and investigated for inhibition of cell proliferation against three cancer cell lines, HT-29, MCF-7, and AGS, and a normal mouse fibroblastic cell line, NIH-3T3, using an MTT assay. The biological study showed that 2-(methylthio) substituted compounds showed little cytotoxic activity against the four cell lines. In contrast, the presence of the 2-(benzylthio) group on the thiazole ring resulted in a significant improvement in cytotoxic activity relative to the 2-(methylthio) substituted derivatives. Furthermore, the inhibition of tubulin polymerization by some potent compounds was evaluated. All the compounds studied were moderate tubulin polymerization inhibitors. The flow cytometry analysis confirmed that the synthesized compounds led to cell cycle arrest at the G2/M phase. Docking simulation was performed to insert these compounds into the crystal structure of tubulin at the colchicine binding site to determine a probable binding model.
Salehi, Marjan,Amini, Mohsen,Ostad, Seyed Nasser,Riazi, Gholam Hossein,Assadieskandar, Amir,Shafiei, Bentolhoda,Shafiee, Abbas
p. 7648 - 7654
(2013)
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On crystal structure investigations of α- and β- ammoniumdithiocarbamate NH4CS2NH2 and the role of hydrogen bonding
Single crystal X-ray data of the low temperature a- and the high temperature β-modifications of NH4CS2NH2 were collected at 170(2) K and at 310(2) K, respectively and the crystal structures were investigated. The a-type crystallizes orthorhombically in the space group Pca21 with a = 8.2290(16), b = 5.6234(11), c = 10.694(2) A, and the β-type monoclinically in space group Cc with a = 14.7968(14), b = 9.4974(6), c = 9.3610(9) A and β = 129.119(9)°. The crystal chemical relations between the two modifications are discussed particularly with regard to the hydrogen-bonding networks.
Teske, Christoph L.,Bensch, Wolfgang
p. 356 - 362
(2010)
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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)

5 - Hydroxy indoles containing heterocyclic ring derivative and its use
The present invention relates to a heterocyclic ring-containing 5-hydroxy indole derivative as represented by formula I, comprising a racemate of the derivative, an optical isomer of same, and a pharmaceutically acceptable salt and/or hydrate thereof, where substituent R1, R2, X, Y, and Z have the meanings as provided in the description. The compound of formula I is applicable in preparing a medicament for treatment and/or prevention of viral infections, and particularly for preparing an anti-hepatitis B virus medicament and anti-influenza virus medicament.
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Paragraph 0187; 0188

(2018/05/03)

Novel tetrazoloquinoline-rhodanine conjugates: Highly efficient synthesis and biological evaluation
In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and Mycobacterium bovis BCG, a small focused library of rhodanine incorporated tetrazoloquinoline has been efficiently synthesized by using [HDBU][HSO4] acidic ionic liquid. The compound 3c found to be promising inhibitor of MTB H37Ra and M. bovis BCG characterized by lower MIC values 4.5 and 2.0 μg/mL, respectively. The active compounds were further tested for cytotoxicity against HeLa, THP-1, A549 and PANC-1 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Again, the synthesized compounds were found to have potential antifungal activity. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target Zmp1 enzyme of MTB H37Ra, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of in vitro and in silico study suggest that these compounds possess ideal structural requirement for the further development of novel therapeutic agents.
Subhedar, Dnyaneshwar D.,Shaikh, Mubarak H.,Nawale, Laxman,Yeware, Amar,Sarkar, Dhiman,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.
supporting information
p. 2278 - 2283
(2016/04/20)

NOVEL COMPOUND, ORGANIC CATION TRANSPORTER 3 DETECTION AGENT, AND ORGANIC CATION TRANSPORTER 3 ACTIVITY INHIBITOR
[Problem] The present invention addresses the problem of providing a novel compound. The present invention also addresses the problem of providing an OCT3 detection agent or an OCT3 activity inhibitor, which comprises the novel compound. [Solution] A compound represented by formula (A), a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof. ????????R1-R2-R3-R4?????(A)
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Paragraph 0675-0676; 0679

(2016/08/17)

Imidoyl dichlorides as new reagents for the rapid formation of 2-aminobenzimidazoles and related azoles
The development of a reagent for the efficient synthesis of five- and six-membered azoles at room temperature is proposed. A variety of substituted 2-aminobenzimidazoles are synthesized in good to excellent yields. The ability to incorporate various protecting groups makes the imidoyl dichloride reagent amenable to a large number of syntheses. The reagent is applied to the total synthesis of the 2-aminobenzimidazole containing carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), from 2-chloro-3-nitropyridine in >60% yield in 6 steps.
Pollock, Julie A.,Kim, Sung Hoon,Katzenellenbogen, John A.
supporting information
p. 6097 - 6099
(2015/10/28)

Synthesis, cytotoxic evaluation, and molecular docking study of 4,5-diaryl-thiazole-2-thione analogs of combretastatin A-4 as microtubule-binding agents
A series of combretastatin A-4 analogs in which cis-olefinic bond replaced by thiazole ring were prepared by reaction of α-bromo-1,2-(p-substituted) diaryl-1-ethanones and dithiocarbamate derivatives. The cytotoxicity of these compounds was determined against three cancer cell lines (HT-29), (MCF-7), (AGS) as well as fibroblastic cell line (NIH-3T3) using MTT assay. Inhibition of tubulin polymerization for some potent compounds was evaluated. These biological studies proved that 6j and 6o were the most potent compounds in this series. Furthermore 2-(methylthio)-substituted compounds show moderate or no activity. Docking studies involving 6j and 6o demonstrated that this analogs could be successfully docked in the colchicine binding site of α,β-tubulin.
Salehi, Marjan,Ostad, Seyed Nasser,Riazi, Gholam Hossein,Assadieskandar, Amir,Cheraghi-Shavi, Tayebeh,Shafiee, Abbas,Amini, Mohsen
p. 1465 - 1473
(2014/03/21)

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)

Synthesis new and novel aryl thiazole derivatives compounds
Six new compounds of Thiazoles family was synthesis from condensation reaction of some compounds from pyrazolines. NMR, IR and elemental analysis was used for identification of these compounds. Position of aliphatic and aromatic hydrogens in pyrazolone and thiazole cycles had established proceeding of identification. Most of obtained compounds like aciform crystals, their color is white and yellow. Reaction time and yield of these compounds had shown better results as compared with other thiazole derivations.
Akbarzadeh, Abolfath,Soleymani, Reza,Taheri, Milad,Ali, Maryam Karimi-Cheshmeh
experimental part
p. 153 - 164
(2012/09/07)

Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists
The discovery, synthesis, and optimization of compound 1 from a high-throughput screening hit to highly potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonists are reported. The synthesis and structure-activity relationship in this series are described in detail. On the basis of a general schematic PPAR pharmacophore model, scaffold 1 was divided into headgroup, linker, and tailgroup and successively optimized for PPAR activation using in vitro PPAR transactivation assays. A (2-methylphenoxy)acetic acid headgroup, a flexible linker, and a five-membered heteroaromatic center ring with two hydrophobic aryl substituents were required for efficient and selective PPARδ activation. The fine-tuning of these aryl substituents led to an array of highly potent and selective compounds such as compound 38c, displaying an excellent pharmacokinetic profile in mouse. In an in vivo acute dosing model, selected members of this array were shown to induce the expression of pyruvate dehydrogenase kinase-4 (PDK4) and uncoupling protein-3 (UCP3), genes that are known to be involved in energy homeostasis and regulated by PPARδ in skeletal muscle.
Epple, Robert,Cow, Christopher,Xie, Yongping,Azimioara, Mihai,Russo, Ross,Wang, Xing,Wityak, John,Karanewsky, Donald S.,Tuntland, Tove,Nguyê?-Tran, Van T. B.,Ngo, Cara Cuc,Huang, David,Saez, Enrique,Spalding, Tracy,Gerken, Andrea,Iskandar, Maya,Seidel, H. Martin,Tian, Shin-Shay
scheme or table
p. 77 - 105
(2010/04/30)

FUSED PYRIDINES ACTIVE AS INHIBITORS OF C-MET
Fused pyridines of formula (I) and the pharmaceutically acceptable salts thereof have activity as inhibitors of c-Met and may thus be used to treat various diseases and disorders including cancer. Processes for synthesizing the compounds are also described
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Page/Page column 35

(2009/09/05)

SULFONAMIDE CONTAINING COMPOUNDS FOR TREATMENT OF INFLAMMATORY DISORDERS
Provided are compounds, pharmaceutical compositions and methods of treatment or prophylaxis of an inflammatory condition, in particular asthma. The compounds are of the general Formula I, or a pharmaceutically acceptable salt, ester, prodrug or derivative thereof: wherein: X and Y are independently selected from-CH2-or-CH2-CH2;Z is seleceted from S(O)m or Se(O)m and m is 0, 1 or 2; R1 is optionally substituted heteroaryl or heterocyclic; R2 is selected from the group consisting of hydrogen, C1 -C6 straight alkyl, and C1 -C6 branched alkyl, wherein all may be optionally substituted; and R3 and R4 are alkyl.
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Page/Page column 90

(2008/12/08)

3- (1,2,4-TRIAZOL-3YLALKYL) AZABRICLO (3.1.0) HEXANE DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS
The present invention relates to novel compounds of formula (I) or pharmaceutically acceptable salt thereof: wherein " G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl and indazolyl; " p is an integer ranging from 0 to 5; " R1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and SF5, or corresponds to a group R5; " each R2 is independently hydrogen, fluorine or C1-4alkyl; " n is 2, 3, 4, or 5; " R3 is C1-4alkyl; " R4 is hydrogen, or a C1-4alkyl group, a benzyl group, a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and SF5;or R4 is a -SR6 group; " R5 is selected from a group consisting of: isoxazolyl, -CH2-N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl and 2-pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from a group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy and C1-4alkanoyl; " R6 is C1-4alkyl or -CH2C3-4cycloalkyl; and when R1 is chlorine and p is 1, such R1 is not present in the ortho position with respect to the linking bond to the rest of the molecule; and when R1 corresponds to R5, p is 1. processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D3 receptors, e.g. to treat drug dependency, as antipsychotic agents, to treat obsessive compulsive spectrum disorders, premature ejaculation or cognition impairment.
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Page/Page column 48

(2008/06/13)

Synthesis of potential plant protecting compounds on the basis of 2,3-dihydrothiazol-2-thione. I. Change in structure at the N3 and C4
A considerable number of potential plant protecting compounds with the core structure of 2,3-dihydrothiazol-2-thione has been prepared by the reaction of dithiocarbamates with halomethylcarbonyl compounds forming N-substituted 4-substituted 4-hydroxythiazolidin-2-thiones 2-4, which can split off water to yield 5. The structural variability at N3 is given either by the amine used for dithiocarbamate synthesis or by acylation of N-unsubstituted 2,3-dihydrothiazol-2-thiones like 4i. The variability at C4 is either achieved by the kind of the halomethylcarbonyl compound or by reactions of 4:chloromethyl derivatives 5, which can be transformed by a number of nucleophilic reagents to derivatives like thioethers 8, ethers 9, amines 10, nitriles 11, azides 12a, thiocyanates 12b, the primary amine 14 and derived from that the amides 15 or the ureas 16. Wiley-VCH Verlag GmbH, 2000.
Hanefeld, Wolfgang,Wurtz, Stephan
p. 355 - 370
(2007/10/03)

An Efficient Synthesis of 1,3-Thiazole
The cyclocondensation of methyl dithiocarbamate with chloroacetaldehyde in aqueous ethanol affords 2-methylthio-1,3-thiazole (82-88percent) which is demethylsulfenylated to 1,3-thiazole (78-81percent) by reaction with lithium in liquid ammonia followed by hydrolysis with aqueous ammonia chloride.
Brandsma, L.,Jong, R. L. P. de,VerKruijsse, H. D.
p. 948 - 949
(2007/10/02)

INVESTIGATION IN THE FIELD OF BIACETYLENE DERIVATIVES. XLII. ADDITION OF AMMONIUM DITHIOCARBAMATES TO BIACETYLENE
A simple method was developed for the production of cis-1-buten-ynyl dialkyldithiocarbamates and 1,4-bis(dialkylthiocarbamoylthio)-1,3-butadienes by the reaction of biacetylene and carbon bisulfide in the presence of secondary amines without a catalyst in protic and aprotic solvents.
Sokolyanskaya, L. V.,Vavilova, A. N.,Volkov, A. N.,Trofimov, B. A.
p. 2025 - 2028
(2007/10/02)