Tag: M.W=150-200

Takahashi, Torizo published the artcilePyridine derivatives containing sulfur. XVII. Synthesis of pyridothiazoles and pyrimidazoles, Application In Synthesis of 31784-71-1, the publication is Yakugaku Zasshi (1946), 66(No. 7/8A), 26, database is CAplus.

By the use of Cu(SCN)₂ in glacial AcOH solution the following 2-aminopyrido[2,3-d]thiazoles were obtained: 6-nitro, yellow plates, m. 183°, from 2-amino-5-nitropyridine; 6-bromo, yellow plates, m. 135°, from 5-bromo-2-amino-pyridine; and 5-chloro, pale yellow needles, m. 69-71°, from 2-chloro-5-aminopyridine. BrCH₂COMe with 5-bromo- or 5-nitro-2-aminopyridine gave 6-bromo-2-methyl-imidazo[1,2-a]pyridine HCl salt, colorless, efflorescent rhomboprisms, and the 6-nitro analog (I), bright yellow needles, m. 161°. Reduction of I gave the corresponding amino compound, colorless needles, m. 77° (N-Ac derivative), colorless needles, m. 181°.

Yakugaku Zasshi 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 C5H6N2O2, Application In Synthesis of 31784-71-1.

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

Hamashima, Y. published the artcileSynthesis, biological properties, and pharmacokinetics of 7432-S, a new oral cephem, Related Products of thiazole, the publication is Special Publication – Royal Society of Chemistry (1989), 77-90, database is CAplus.

A number of cephems with ω-carboxyalkenoylamino substituents were prepared and tested for antibacterial activity and oral absorbability. Of these derivatives, the cephem with 7β-(2-(2-amino-4-thiazolyl)-4-carboxy-2-butenoyl)amino] substituent were well absorbed in mice. 7432-S (I) was finally selected as the clin. candidate having antibacterial activity and excellent oral bioavailability.

Special Publication – Royal Society of Chemistry published new progress about 64987-16-2. 64987-16-2 belongs to thiazole, auxiliary class Thiazole,Amine,Ester, name is Methyl 2-(2-aminothiazol-4-yl)acetate, and the molecular formula is C6H8N2O2S, Related Products of thiazole.

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

Haroun, Michelyne published the artcileIn Silico Design, Synthesis and Evaluation of Novel Series of Benzothiazole- Based Pyrazolidinediones as Potent Hypoglycemic Agents, Formula: C7H5ClN2S, the publication is Medicinal Chemistry (Sharjah, United Arab Emirates) (2020), 16(6), 812-825, database is CAplus and MEDLINE.

The discovery of novel ligand binding domain (LBD) of peroxisome proliferator- activated receptor γ (PPARγ) has recently attracted attention to few research groups in order to develop more potent and safer antidiabetic agents. This study is focused on docking-based design and synthesis of novel compounds combining benzothiazole and pyrazolidinedione scaffold as potential antidiabetic agents. Several benzothiazole-pyrazolidinedione hybrids were synthesized and tested for their in vivo anti-hyperglycemic activity. Interactions profile of title compounds against PPARγ was examined through mol. modeling approach. All tested compounds exhibited anti-hyperglycemic activity similar or superior to the reference drug Rosiglitazone. Introducing chlorine atom and alkyl group at position-6 and -5 resp. on benzothiazole core resulted in enhancing the anti-hyperglycemic effect. Docking study revealed that such groups demonstrated favorable hydrophobic interactions with novel LBD Ω – pocket of PPARγ protein. Among the tested compounds, N-(6-chloro-5-methylbenzo[d]thiazol-2-yl-4-(4((3,5- dioxopyrazolidin-4-ylidene)methyl)phenoxy)butanamide) 5b was found to be the most potent compound and provided valuable insights to further develop novel hybrids as anti-hyperglycemic agents.

Medicinal Chemistry (Sharjah, United Arab Emirates) 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, Formula: C7H5ClN2S.

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

Okafor, Charles O. published the artcileThe first branched benzoxazinophenothiazine ring system and its aza analogs, Application of 5-Chlorothiazolo[5,4-b]pyridin-2-amine, the publication is Tetrahedron (1988), 44(4), 1187-94, database is CAplus.

The synthesis of a branched benzoxazinophenothiazine heterocycle is described. The parent compound benzo[a][1,4]-benzoxazino[3,2-c]phenothiazine (I), was obtained from 2,3-dichloro-1,4-naphthoquinone, 2-aminophenol and 2-(amino)thiophenol. Monoaza-, diaza- and triaza- analogs of this novel heterocycle were also synthesized. The parent compounds, 16-oxa-15-thia-4,5,10-triazabenzo[h]pentaphene and 16-oxa-15-thia-4,5,10,14-tetraazabenzo[h]pentaphene were also synthesized as well as 4-amino-16-oxa-15-thia-4,5,10,12,14-pentaazabenzo[h]pentaphene. They are intensely colored high-melting solids suitable for application as pigments. Their ease of reduction with Na₂S₂O₄ and the ready oxidation of the reduced compounds to the quinoid forms by atm. oxygen suggest their applicability also as vat dyes.

Tetrahedron 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, Application of 5-Chlorothiazolo[5,4-b]pyridin-2-amine.

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

Okafor, Charles O. published the artcileHeterocyclic series. II. 3,6-Diazaphenothiazine sulfoxides and other potential antiparasitic and pesticidal agents, Application In Synthesis of 31784-71-1, the publication is Journal of Chemical and Engineering Data (1971), 16(2), 244-6, database is CAplus.

New derivatives of thiazolo[5,4-b]pyridine (I) and 3,6-diazaphenothiazine (II) are described. The yields of products spotlight a definite trend in the role of substituents in the conversion of pyridine derivatives to thiazolo[5,4-b]pyridines. Some derivatives of these compounds were hydrolyzed and converted to nitrothienyl pyridyl sulfides of antibacterial and pesticidal interests by reacting with 2-bromo-3,5-dinitrothiophene. The latter similarly reacts with aminopyridines to yield thienyl aminopyridines. In an attempt to convert 7-methoxy- and 7-chloro-1-nitro-3,6-diazaphenothiazines to their dinitro-3,6-diazaphenothiazine derivatives, only 7-methoxy- and 7-chloro-1-nitro-3,6-diazaphenothiazine sulfoxides, identified by their strong sulfoxide band in the 1035-to 1045-cm-1 region, were obtained.

Journal of Chemical and Engineering Data 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, Application In Synthesis of 31784-71-1.

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

Okafor, Charles O. published the artcileHeterocyclic series. VII. Use of Kaufmann’s reaction as a route to o-aminomercaptopyridines, COA of Formula: C6H4ClN3S, the publication is Journal of Organic Chemistry (1973), 38(26), 4383, database is CAplus.

Kaufmann thiocyanation of 6-substituted 2-amino- and 3-aminopyridines gave 6-substituted-2-amino-3-thiocyanatopyridine (I) and 5-substituted-2-aminothiazolo[5,4-b]pyridine (II), resp. The action of 20% NaOH on II led to 6-substituted 3-aminopyridine-2(1H)-thiones. Heating I in Ac2O gave 5-substituted 2-acetamidothiazolo[4,5-b]pyridine.

Journal of Organic 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, COA of Formula: C6H4ClN3S.

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

Ueda, Kanichi published the artcilePyridine derivatives containing sulfur. L. Mechanism of cleavage of thiazole ring of 2-aminothiazolo[5,4-b]pyridines by means of aqueous alkali, Application In Synthesis of 31784-71-1, the publication is Pharmaceutical Bulletin (1956), 396-401, database is CAplus and MEDLINE.

cf. C.A. 51, 2741i. Determination of the structures of the previously reported (C.A. 48, 5187h) “Substances I (I), II (II), and III (III),” prepared from 6-Cl (IV) and 6-EtO (V) derivatives of 3-amino-2-mercaptopyridine should help clarify the mechanism of the cleavage of the thiazole ring of the title compounds Comparisons of the infrared and ultraviolet absorption spectra of I with those of the 3-amino (VI) and 3-acetamido (VII) derivatives of 6,2-Cl(MeS)C₅H₂N (VIII) led to the conclusion that I was 6,2,3-Cl(MeS)(H₂NCONH)C₅H₂N. This conclusion was supported by heating 0.6 g. I 6 hrs. on a H₂O bath with 40 cc. Ac₂O and evaporating in vacuo to give 0.08 g. 3-AcNHCONH derivative of VIII, m. 209°, and 0.3 g. VII, m. 166° (from the mother liquor chromatographed in CHCl₃ over Al₂O₃). Support also came from the synthesis of I:1.2 g. IV in 170 cc. AcOH treated slowly with 2.5 g. KNCO in 20 cc. H₂O at 40°, stirred 3 hrs., diluted with much H₂O, and kept overnight yielded 0.82 g. 6,2,3-Cl(HS)(H₂NCONH)C₅H₂N (IX), m. 185-90° (effervescence); this gave I, m. 286-95°, methylated with MeI in alk. solution Also, 0.8 g. VI similarly treated with KNCO yielded 0.8 g. I. Likewise treated with KNCO, 2-MeS (X) and 2-EtS derivatives of 3,6-H₂N(EtO)C₅H₃N gave II, m. 200-36°, and III, m. 160-1°, resp.; their ultraviolet spectra confirmed their structures as 6,2,3-EtO(MeS)(H₂NCONH)C₅H₂N and 6,2,3-EtO(EtS)(H₂NCONH)C₅H₂N, resp. The mechanism of cleavage of the thiazole ring in the 5-Cl (XI) and 5-EtO (XII) derivatives of the title compound was studied. XI (0.7 g.) was refluxed 1 hr. in an oil bath at 120-30° with 6 cc. 10% NaOH while NH₃ evolved, the solution neutralized with AcOH, the resulting precipitate methylated with Me₂SO₄, the ether extract of the product evaporated, and the residue fractionally crystallized to give 0.21 g. VI, m. 56° (from petr. ether-ether), and 0.22 g. I, m. 290° (from MeOH). However, refluxing 7 hrs. instead of 1 hr. gave only VI. IX (0.7 g.) similarly hydrolyzed for 1 hr. and methylated yielded 0.15 g. VI and 0.12 g. I, but after 6 hrs. hydrolysis it gave only VI. XII (1 g.) refluxed 6.5 hrs. with 10 cc. 20% NaOH in the presence of 0.2 g. As₂O₃ while NH₃ evolved, the mixture cooled, filtered, and the filtrate neutralized with AcOH yielded 0.7 g. V, m. 150-70° (characterized by methylation to X and acetylation to 3,6,2-AcNH(EtO)(MeS)C₅H₂N, m. 124°), and after standing overnight, 0.1 g. 6,2,3-EtO(HS)(H₂NCONH)C₅H₂N, m. 195-8° (decomposition)(characterized by methylation with Me₂SO₄ to II). Longer hydrolysis (10 hrs.) of XII gave only V. Confirmation of the production of V from XII was obtained by condensing it (0.5 g.) in 1 cc. H₂O and 5 cc. EtOH containing 0.2 g. NaOH with 0.6 g. BzCH₂Br to yield, after standing overnight at room temperature, the expected 6-ethoxy-2-phenylpyrido[2,3-b]1,4-thiazine(0.42 g.), m. 125° (C.A. 50, 10101g). These results of hydrolysis of IX, XI, and XII led to the conclusion that amino-thiazolopyridines were converted to mercaptopyridines through mercaptopyridylureas as intermediates, which were somewhat resistant to the hydrolysis.

Pharmaceutical Bulletin 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 C11H10ClNO, Application In Synthesis of 31784-71-1.

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

Jiang, Chen Hao published the artcileBioinformatics-based screening of key genes for transformation of liver cirrhosis to hepatocellular carcinoma, Computed Properties of 95-24-9, the publication is Journal of Translational Medicine (2020), 18(1), 40, database is CAplus and MEDLINE.

Abstract: Background: The aims of the present study were to identify key genes related to the transformation of cirrhosis into HCC, and explore the associated mol. mechanisms. Methods: GSE89377, GSE17548, GSE63898 and GSE54236 mRNA microarray datasets from Gene Expression Omnibus (GEO) were analyzed to obtain differentially expressed genes (DEGs) between HCC and liver cirrhosis tissues, and network anal. of protein-protein interactions (PPIs) was carried out. String and Cytoscape were used to analyze modules and identify hub genes, Kaplan-Meier Plotter and Oncomine databases were used to explore relationships between hub genes and disease occurrence, development and prognosis of HCC, and the mol. mechanism of the main hub gene was probed using Kyoto Encyclopedia of Genes and Genomes(KEGG) pathway anal. Results: In total, 58 DEGs were obtained, of which 12 and 46 were up- and down-regulated, resp. Three hub genes (CDKN3, CYP2C9 and LCAT) were identified and associated prognostic information was obtained. CDKN3 may be correlated with the occurrence, invasion, and recurrence of HCC. Genes closely related to changes in the CDKN3 hub gene were screened, and Kyoto Encyclopedia of Genes and Genomes (KEGGs) pathway anal. identified numerous cell cycle-related genes. Conclusion: CDKN3 may affect the transformation of liver cirrhosis into HCC, and represents a new candidate mol. marker of the occurrence and progression of HCC.

Journal of Translational Medicine 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, Computed Properties of 95-24-9.

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

Jamal Gilani, Sadaf published the artcileNovel benzothiazole hydrazine carboxamide hybrid scaffolds as potential in vitro GABA AT enzyme inhibitors: Synthesis, molecular docking and antiepileptic evaluation, Computed Properties of 95-24-9, the publication is Bioorganic & Medicinal Chemistry Letters (2019), 29(14), 1825-1830, database is CAplus and MEDLINE.

In the present study, a series of newer benzothiazole derivatives containing thiazolidin-4-one and azetidin-2-one, were synthesized by the cyclization of benzothiazolyl arylidene hydrazine carboxamide derivatives with thioglycolic acid and chloroacetyl chloride, resp. Results of in vivo anticonvulsant screening revealed that compounds I (R = 2,4-Cl₂, 4-NO₂) and II (R = 4-NO₂) have promising anticonvulsant activities without any neurotoxicity. Selected compounds were also evaluated for their in vitro GABA AT inhibition. The results indicated that compound I (R = 2,4-Cl₂, IC₅₀ 15.26 μM) exhibited excellent activity as compared to the standard drug vigabatrin (IC₅₀ 39.72 μM) suggesting the potential of these benzothiazole analogs as new anticonvulsant agents.

Bioorganic & Medicinal Chemistry Letters 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, Computed Properties of 95-24-9.

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

Koperniku, Ana published the artcileThe Reaction of N -Trimethylsilyl-Substituted Heteroarylamines with Esters and Thioesters: An Efficient Protocol To Access Diheteroarylamides, Quality Control of 95-24-9, the publication is Synthesis (2019), 51(8), 1779-1790, database is CAplus.

The S-benzyl thioester and Me ester derivatives of a representative 4-pyridinone-based carboxylic acid were sufficiently activated to react efficiently in amide coupling reactions with the amide anion generated in situfrom the N-trimethylsilyl derivative of different weakly nucleophilic heteroarylamines. In acetonitrile as solvent, the precipitated diheteroarylamide products were isolated in pure form by vacuum filtration. This simple amide bond forming protocol can be readily adapted to the parallel synthesis of compound libraries.

Synthesis 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, Quality Control of 95-24-9.

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