Category: thiazole

Acar Cevik, Ulviye published the artcileSynthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors, Application of 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Heterocyclic Chemistry (2020), 57(5), 2225-2233, database is CAplus.

In this study, a novel series of benzothiazole-thiadiazole I (R¹ = Et, methoxyethyl, n-Pr, n-Bu; R² = H, Cl, NO₂) was synthesized. These compounds I were evaluated as inhibitors for types A and B MAO enzymes. Compounds I [(A), R¹ = methoxyethyl, R² = NO₂; R¹ = n-Bu, R² = NO₂, (B)] were the most active derivatives in the series with IC₅₀ values of 0.107 ± 0.003 and 0.128 ± 0.004, resp. Furthermore, compounds (A) and (B) were investigated for their cytotoxicity and found as non-cytotoxic.

Journal of Heterocyclic Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Application of 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Fleau, Charlotte published the artcileChagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series, COA of Formula: C7H5ClN2S, the publication is Journal of Medicinal Chemistry (2019), 62(22), 10362-10375, database is CAplus and MEDLINE.

Acylaminobenzothiazole hits were identified as potential inhibitors of T. cruzi replication, a parasite responsible for Chagas Disease. We selected compound 1, N-(6-chlorobenzo[d]thiazol-2-yl)cyclopropanecarboxamide, for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.630μM) and its human metabolic stability (human clearance = 9.57mL/min/g). A total of 39 analogs of 1 were synthesized and tested in vitro. We established a multiparametric structure activity relationship, allowing optimization of both anti-parasite activity, physicochem. parameters and ADME properties. We identified compound 50, N-(5-Fluoro-6-(trifluoromethyl)benzothiazol-2-yl)cyclopropanecarboxamide, as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079μM), an enhanced metabolic stability (Human Clearance = 0.413mL/min/g) and opportunity for oral route of administration. After tolerability assessment, compound 50 demonstrated a promising in vivo efficacy.

Journal of Medicinal Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, COA of Formula: C7H5ClN2S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Rao, Ashwin U. published the artcileSynthesis and structure-activity relationships of 2-(1,4′-bipiperidin-1′-yl)thiazolopyridines as H₃ receptor antagonists, SDS of cas: 31784-71-1, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(21), 6176-6180, database is CAplus and MEDLINE.

A series of 2-(1,4′-bipiperidin-1′-yl)thiazolopyridines I (X = N, Y = CH; X = CH, Y = N; R = H, H₂N, CN, Cl, MeCONH, 4-NCC₆H₄, 2-fluoro-3-pyridyl, 5-pyrimidyl, etc.) was synthesized and evaluated as a new lead of non-imidazole histamine H₃ receptor antagonists. Introduction of diversity at the 6-position of the pyridine ring was designed to enhance in vitro potency and decrease hERG activity. The structure-activity relationships for these new thiazolopyridine antagonists are discussed.

Bioorganic & Medicinal Chemistry Letters published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, SDS of cas: 31784-71-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Stanciauskaite, Monika published the artcileComparison of Ethanolic and Aqueous Populus balsamifera L. Bud Extracts by Different Extraction Methods: Chemical Composition, Antioxidant and Antibacterial Activities, Safety of Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Pharmaceuticals (2021), 14(10), 1018, database is CAplus and MEDLINE.

The balsam poplar (Populus balsamifera L.) buds that grow in Lithuania are a polyphenol-rich plant material with a chem. composition close to that of propolis. In order to potentially adapt the extracts of this plant’s raw material for therapeutic purposes, it is important to carry out detailed studies on the chem. composition and biol. activity of balsam poplar buds. An important step is to evaluate the yield of polyphenols by different extraction methods and using different solvents. According to our research, extracts of balsam poplar buds collected in Lithuania are dominated by p-coumaric (496.9-13,291.2μg/g), cinnamic acid (32.9-11,788.5μg/g), pinobanksin (34.9-1775.5μg/g) and salicin (215.3-1190.7μg/g). The antioxidant activity of poplar buds was evaluated by the ABTS (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)), DPPH (2,2-diphenyl-1-picrylhydrazyl) and FRAP (ferric-reducing antioxidant power) methods, all extracts showed antioxidant activity and the obtained results correlated with the obtained amounts of total phenolic compounds in the extracts (ABTS r = 0.974; DPPH r = 0.986; FRAP r = 0.955, p <0.01). Studies of antimicrobial activity have shown that ethanolic extracts have an antimicrobal activity effect against Staphylococcus aureus, Enterococcus faecalis and Escherichia coli. The extracts showed a better antimicrobal activity against gram-pos. bacteria.

Pharmaceuticals published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C20H12N2O2, Safety of Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate).

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Moodley, Rashmika published the artcileNew Quinoline-Urea-BenzΞothiazole Hybrids as Promising Antitubercular Agents: Synthesis, In Vitro Antitubercular Activity, Cytotoxicity Studies, and In Silico ADME Profiling, Product Details of C7H5ClN2S, the publication is Pharmaceuticals (2022), 15(5), 576, database is CAplus and MEDLINE.

A series of 25 new benzothiazole-urea-quinoline hybrid compounds, I (X = H, Me, F, NO₂, etc.) and II (n = 0, 2, 3, 4, and 6) were synthesized successfully via a three-step synthetic sequence involving an amidation coupling reaction as a critical step. In vitro evaluation of these hybrid compounds for their antitubercular inhibitory activity against the Mycobacterium tuberculosis H37Rv pMSp12::GPF bioreporter strain was undertaken. Of the 25 tested compounds, 17 compounds exhibited promising anti-TB activities of less than 62.5μM (MIC90) and 13 compds showed promising activity with MIC90 values in the range of 1-10μM, while compound I(X = CF₃), being the most active, exhibited sub-micromolar activity (0.968μM) in the CAS assay. In addition, minimal cytotoxicity against the HepG2 cell line (cell viability above 75%) in 11 of the 17 compounds, at their resp. MIC90 concentrations, was observed, with compound I(X = CF₃), exhibiting 100% cell viability. The hybridization of the quinoline, urea, and benzothiazole scaffolds demonstrated a synergistic relationship because the activities of resultant hybrids were vastly improved compared to the individual entities. In silico ADME predictions showed that the majority of these compounds have drug-like properties and are less likely to potentially cause cardiotoxicity (QPlogHERG > -5).

Pharmaceuticals published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Product Details of C7H5ClN2S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kallur, H. J. published the artcileSynthesis, characterization and anthelmintic screening of some new benzothiophene derivatives, Application In Synthesis of 95-24-9, the publication is World Journal of Pharmaceutical Research (2020), 9(5), 1838-1849, database is CAplus.

The proposed work was carried out by following Schemes. In the Scheme-I the starting material cinnamic acid was reacted with thionyl chloride, in presence of pyridine in chlorobenzene medium to yield 3- chlorobenzo[b]thiophene-2-carbonylchloride. Where as in the Scheme-II the 2-amino-6-substituted benzothiazoles I (R = Me, COOEt, Cl, OMe, F, nitro) was prepared by the reaction of 4-substituted anilines 4-RC₆H₄NH₂ and potassium thiocyanate in presence of bromine in acetic acid. In the scheme-III, the compound N-(6-substituted-1,3-benzothiazol-2-yl)-3-chloro-1-benzothiophene-2-carboxamides II was prepared by reacting 3-chlorobenzo[b]thiophene-2-carbonylchloride and 2-amino-6-substituted benzothiazoles I in pyridine medium refluxed for 10-15 h. The synthesized compounds II were evaluated for the anthelmintic activity.

World Journal of Pharmaceutical Research published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Application In Synthesis of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Belaidi, Salah published the artcileElectronic structure and physico-chemical property relationship for thiazole derivatives, Synthetic Route of 31784-71-1, the publication is Asian Journal of Chemistry (2013), 25(16), 9241-9245, database is CAplus.

Electronic structure, effect of the substitution and structure physico-chem. property relationship for thiazole derivatives, has been studied by ab initio and DFT method. In the present work, the calculated values, i.e., net charges, bond lengths, dipole moments, electron-affinities, heats of formation and QSPR properties, are reported and discussed in terms of the reactivity of thiazole derivatives

Asian Journal of Chemistry published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, Synthetic Route of 31784-71-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Lynch, Daniel E. published the artcileThe hydrogen-bonding networks of 2-amino-4-phenyl-1,3-thiazole derivatives, Recommanded Product: 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Crystal Engineering (2002), 5(2), 123-136, database is CAplus.

The solid-state packing arrays of nine 4-Ph substituted 2-amino-1,3-thiazoles were examined and their H-bonding networks discussed. The nine compounds, in addition to 2-amino-1,3-thiazole 1, were 2-amino-4-phenyl-1,3-thiazole 2, 2-amino-4-phenyl-1,3-thiazolium bromide monohydrate 3, Et 2-amino-4-phenyl-1,3-thiazole-5-carboxylate 4, 2-amino-4-(3-coumarin)-1,3-thiazole 5, 2-amino-4-(4-methylphenyl)-1,3-thiazole 6, 2-amino-4-(2-hydroxyphenyl)-1,3-thiazole 7, 2-amino-4-(4-bisphenyl)-1,3-thiazole 8, 2-amino-4-(1-naphthyl)-1,3-thiazole 9, and 2-amino-4-(2-naphthyl)-1,3-thiazolium bromide 10. The single-crystal x-ray structures of 1-5 were previously reported while the structures of 6-10 are presented. A variety of different packing motifs are observed with only four (4, 5, 6 and 9) exhibiting the characteristic R₂²(8) H-bonded 2-amino-1,3-thiazole dimers. In two of these four structures (6 and 9) potential N-H…π H-bonding interactions exist whereas all remaining structures exhibit a combination of N-H…N with either N-H…O, N-H…S or N-H…Br associations in their H-bonding networks.

Crystal Engineering published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C13H10N2S, Recommanded Product: 4-(Naphthalen-1-yl)thiazol-2-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Chanon, Michel published the artcileUltraviolet, infrared, and nuclear magnetic resonance study of 4-thiazoline-2-thiones and of their 2-alkylthiothiazole isomers. The protomeric problem, COA of Formula: C4H5NS2, the publication is Bulletin de la Societe Chimique de France (1968), 2868-80, database is CAplus.

The uv spectra of the title materials were analyzed for protomeric thiol-thione in mols. in the neutral state, solvent effect, and proton fixation. The N.M.R. spectra showed a thiol-thione equilibrium, the effect of substituents, and the presence of ionized mols. The spectral characteristics in various ir regions were examined for use in the protomeric study. The advantages and disadvantages of each method used were assessed.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, COA of Formula: C4H5NS2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Vernin, Gaston published the artcileThin-layer and gas chromatography of thiazole and benzothiazole heterocycles, Synthetic Route of 5053-24-7, the publication is Bulletin de la Societe Chimique de France (1967), 846-56, database is CAplus.

Compounds of the general formula I, II, and III were prepared according to known methods and the effect of different factors on their mobility was studied. The following were prepared (I, R, R1, R2, and b.p. given): H, H, H, 117-18°; Me, H, H, 128-30°; Et, H, H, 148°; H, Me, Me, 133°; H, Et, H, 145°; H, iso-Pr, H, 171°; H, H, Me, 141°; H, H, Et, 162°; Me, Me, H, 145°; Me, H, Me, 149°; H, Me, Me, 158°; iso-Pr, H, H, 160°; Pr, H, H, 175°; iso-Bu, H, H, 172°; tert-Bu, H, H, 180°; neopentyl, H, H, 198°; Cl, H, H, 142°; Br, H, H, b20 69-71°; iso-Pr, Me, H, b50 92°; tert-Bu, Me, H, b50 96°; Me, tert-Bu, H, b50 96°; Et, tert-Bu, H, b50 108°; iso-Pr, tert-Bu, H, b50 113°; tert-Bu, tert-Bu, H, b50 114°; MeS, H, H, -; EtS, H, H, -; PrS, H, H, -; iso-PrS, H, H, -; tert-BuS, H, H, -; iso-Bu, H, H, -; PhCH2S, H, H, -; SH, H, H, -; SH, Me, H, -; SH, H, Me, -; MeS, H, H, -, SH, Me, Me, -; MeS, Me, H, -; MeS, Me, Me, -; SH, Ph, H, -; (II, R, R1, and R2 given): H, H, H; H, Me, H; H, H, Me; Me, H, H; H, Me, Me; Me, Me, H; Me, Me, Me; H, Ph, H; and (III, R and b.p. given): H, 231°; Me, 240°; Et, 252°; Pr, 256°; iso-Pr, 261°; iso-Bu, 269°; tert-Bu, b16 138°; neopentyl, -, m. 52°. Thin-layer chromatog. gives a better separation than gas phase chromatog. for the 2-Me, 2-Ph, 4-Me, 4-Ph, and 2,4-di-Me compounds The mobility of methylthiazoles decreases in the following manner: 4-Me > 5-Me > 2-Me; polar effects are similar for the groups: Et, iso-Pr, and tert-Bu. Steric effects become important for the groups iso-Pr and tert-Bu.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C15H14Cl2S2, Synthetic Route of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica