Heterocyclic Building Blocks-Thiazole

Iwasaki, Masayuki published the artcilePalladium-Catalyzed Regio- and Stereoselective Carbothiolation of Terminal Alkynes with Azolyl Sulfides, Synthetic Route of 5053-24-7, the publication is Organic Letters (2016), 18(7), 1642-1645, database is CAplus and MEDLINE.

Palladium-catalyzed carbothiolation of terminal alkynes with azolyl sulfides affords various 2-(azolyl)alkenyl sulfides with perfect regio- and stereoselectivities. The present addition reaction proceeded through a direct cleavage of carbon-sulfur bonds in azolyl sulfides. The resulting adducts that are useful intermediates in organic synthesis are further transformed to multisubstituted olefins containing azolyl moieties.

Organic Letters 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, Synthetic Route of 5053-24-7.

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

Ukrainets, I. V. published the artcile4-Hydroxy-2-quinolones 148. Synthesis and antitubercular activity of 1-hydroxy-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid N-R-amides, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2008), 44(8), 956-966, database is CAplus.

A method for the synthesis of the title compound [i.e., 1-hydroxy-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid N-amides] is reported here. A reaction of 1,2,3,4-tetrahydroquinoline with methanetricarboxylic acid 1,1,1-tri-Et ester provided an ester compound [i.e., 2,3-dihydro-7-hydroxy-5-oxo-1H,5H-benzo[ij]quinolizine-6-carboxylic acid Et ester]. The above-mentioned amides were prepared from this intermediate by a reaction with primary amines. A comparative anal. has been carried out of the antitubercular activity of the compounds thus prepared with active structural analogs.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C26H26N4O7, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

O’Shea, Jonathan published the artcileAn efficient deprotection method for 5′-[O,O-bis(pivaloyloxymethyl)]-(E)-vinylphosphonate containing oligonucleotides, Safety of N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, the publication is Tetrahedron (2018), 74(42), 6182-6186, database is CAplus.

5′-(E)-Vinylphosphonate (VP) is an effective bioisostere of the natural 5′-monophosphate in small interfering RNAs (siRNAs). Solid-phase synthesis of VP-siRNAs requires the use of appropriately protected VP-phosphoramidites in combination with optimal oligonucleotide deprotection conditions. Addition of 3% (v) neat diethylamine to the standard aqueous ammonia deprotection conditions allows clean and rapid one-step deprotection of 5′-[O,O-bis(pivaloyloxymethyl)] (POM)-protected VP oligonucleotides, minimizing side reactions and impurities, which broadly enhances the scope of VP oligonucleotide synthesis.

Tetrahedron published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C5H7N3S3, Safety of N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide.

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

Millard, B. J. published the artcileHigh resolution mass spectrometry. II. Substituted benzothiazoles, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Organic Mass Spectrometry (1968), 1(2), 285-94, database is CAplus.

The mass spectra of 19 substituted benzothiazoles have been recorded and the identity of the various ions in the mass spectra has been established by high resolution (accurate) mass measurement. Deuterium labeling has been used to elucidate the fragmentation processes of these compounds The parent compound of the series, benzothiazole, exhibits the loss of HCN and CS from the parent ion as the most important decomposition pathways. The H atom concerned in the loss of HCN originates from the 2-position of benzothiazole, while in 2-substituted benzothiazoles, different mechanisms are apparent for the loss of HCN, and these are clarified by D labeling. Some substituted benzothiazoles can lose S from their mol. ions, a process which does not occur in benzothiazole itself. The substituted benzothiazoles undergo many other types of fragmentations, in some cases retaining the substituent, and in other cases losing it prior to collapse of the thiazole ring.

Organic Mass Spectrometry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Xiang, Jiawei published the artcileSynthesis and biological evaluation of innovative thiourea derivatives as PHGDH inhibitors, Application of 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Chemical Papers (2020), 74(11), 3873-3886, database is CAplus.

Abstract: In order to discover novel compounds with inhibitory activity against 3-phosphoglycerate dehydrogenase (PHGDH), a series of thiourea derivatives were designed and synthesized based on the structural modification of compound 5d. Compound 5d emerged from the visual database of ChemDiv of 200,000 small mols. by docking score ranking. Inhibition experiments on PHGDH activity of newly synthesized compounds were performed in vitro. Compounds with more than 30% inhibitory rate at 25μM on PHGDH were screened for IC₅₀ measurement. Anti-proliferative activity of 4a, 5a, 6e, 6n against A2780, MDA-MB-468, MDA-MB-231 and HEK293T in vitro was evaluated. The results showed that the compound 4a displayed the best inhibitory activity on PHGDH among the newly synthesized compounds, and the compounds 4a, 5a, 6n had a better proliferation inhibition effect on human A2780 cell line than NCT-503 reported previously. In addition, 2D interaction diagrams revealed potential action modes of active compounds with PHGDH.

Chemical Papers 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 C40H35N7O8, Application of 4-(Naphthalen-1-yl)thiazol-2-amine.

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

Lin, Xuanfu published the artcileSynthesis and fungicidal activities of 2-benzylthio(sulfonyl)-5-methyl-7-substituted benzyloxy-1,2,4-triazolo[1,5-a] pyrimidine derivatives, Formula: C4H3Cl2NS, the publication is Youji Huaxue (2013), 33(2), 353-358, database is CAplus.

Using 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a]pyrimidine as starting material, twelve novel 2-benzylthio-5-methyl-7-substituted benzyloxy-1,2,4-triazolo[1,5-a]pyrimidine derivatives and their sulfonyl analogs were synthesized through sequential reactions of etherification and oxidation, resp. Their structures were characterized by ¹H NMR, IR, MS and elemental anal. The preliminary bioassay indicated that some compounds exhibited certain fungicidal activities, for example, the inhibition rates of compounds 5c, 5k and 5l (50 μg/mL) against Botrytis cinerea were 61%, 69% and 85%, resp.

Youji Huaxue published new progress about 50398-77-1. 50398-77-1 belongs to thiazole, auxiliary class Thiazoles, name is 5-Chloro-2-(chloromethyl)-1,3-thiazole, and the molecular formula is C4H3Cl2NS, Formula: C4H3Cl2NS.

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

Noman, Efaq published the artcileDecolourisation of dyes in greywater by mycoremediation and mycosorption process of fungi from peatland; primary study, Application In Synthesis of 30931-67-0, the publication is Materials Today: Proceedings (2020), 31(Part_1), 23-30, database is CAplus.

The current study investigated the potential of fungi from peatland for decolorizing dyes in the artificial greywater as a function of oxidative enzymes which included laccase (Lac), manganese peroxidase (MnP), lignin peroxidase (LiP). The fungal isolates were obtained from the peatland on potato dextrose agar (PDA) and purified using single spore technique. Remazol Brilliant Blue R (RBBR), Methylene blue (MB) and Congo red (CR) were used as models for detecting the applicability of the fungal enzyme to decolorizing the dyes. The screening of fungal isolates for the decolorisation of RBBR, MB and CR were investigated using plate assay and liquid-phase assays. The results revealed the fungal isolates varied in their ability to produce oxidative enzymes dependent on the production medium. However, the decolorisation of RBBR in the PD broth medium ranged from 17.96 to 44.89% after 7 days, while ranged from 55.98 to 99.99% in artificial greywater after 15 days of the incubation period. The fungal isolates exhibited also differences in the production of oxidative enzyme. The maximum production of Lac in artificial greywater was recorded by Cochliobolus sp. Number 403 while the highest production of MnP and LiP was noted by Trichoderma sp. Number 102, and Aspergillus sp. Number 506, resp. However, Aspergillus sp. Number 605 was used for further studies, because the fungus exhibited ability to produce Lac, MnP and LiP enzymes simultaneously. It can be concluded that the fungal isolates obtained from the peatland has a potential to decolorize the dyes in the artificial greywater.

Materials Today: Proceedings 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 C18H24N6O6S4, Application In Synthesis of 30931-67-0.

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

Yamamoto, Yuzuru published the artcilePyridine derivatives containing sulfur. XXXI. Synthesis of pyridothiazoles and pyridoxazoles, Application In Synthesis of 31784-71-1, the publication is Yakugaku Zasshi (1951), 169-72, database is CAplus.

cf. C.A. 46, 112h. The following correction is made: 2-Amino-5-bromo- or 2-amino-5-iodopyridine and KCNS or Cu(CNS)₂ do not form a pyridothiazole ring as reported (cf. C.A. 46, 111c, 112ad). To 2-chloro-5-aminopyridine (I) (3 g.) and 9.1 g. KCNS in 47 mL. 95% AcOH at -5 to -10° is added 1.26 g. Br dropwise, the mixture filtered, and 3 volumes H₂O is added to the filtrate, which is again filtered and neutralized with Na₂CO₃ to give crude 2-amino-5-chloropyrido[3,2-d]thiazole (H) (C.A. numbering). Crude II recrystallized from MeOH gives 1.7 g. II, decompose 243-4°. 2-Hydroxy-5-aminopyridine and KCNS and Br in a similar way give the 5-HO analog (III) of II, m. 248-9°; acetate, needles, m. 286°. By using the 2-alkoxy analogs of I the following 5-alkoxy analogs of II are prepared similarly: MeO, needles or plates, m. 191-1.5°; EtO, needles or plates, m. 201-3°; iso-PrO, light yellow plates, m. 191-3°; BuO, plates, m. 139°; and iso-AmO, light orange needles, m. 126.5°. 2,5-Diaminopyridine and KCNS in 95% AcOH similarly give 2,5-diaminopyrido[3,2-d]-thiazole, m. 214-15°. 2,6-Diaminopyridine (3 g.) and 11 g. Cu(CNS)₂ in AcOH after removal of the AcOH, solution of the residue in hot water, and precipitation with Na₂CO₃ give 0.8 g. 2,5-diaminopyrido[2,3-d]thiazole, yellow prisms, m. 137°. Treating 2 g. 2-amino-3-nitro-5-bromopyridine (IV) with 2.8 g. PCl₅ 4 h. at 120-40°, decomposing the excess PCl₅ with ice water, filtering, and recrystallizing from MeOH give 1.4 g. 2-chloro-3-nitro-5-bromopyridine, yellow needles, m. 67-8°. Heating 1.5 g. IV in 6.5 mL. 85% HCl, adding 6.5 g. SnCl₂ at 100° during a period of 3 h., drying in vacuo, making alk. with NaOH, and taking up with ether gives 0.5 g. 2-hydroxy-3-amino-5-bromopyridine (V), m. 182-4°. Boiling 0.5 g. V in 3 mL. Ac₂O 40 min., filtering off the excess Ac₂O, cooling, making alk. with Na₂CO₃, and taking up with AcOEt gives 0.3 g. 6-bromo-2-methyloxazolo[5,4-b]-pyridine, needles, m. 223-5°.

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 C28H29NO4, Application In Synthesis of 31784-71-1.

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

Bort, Guillaume published the artcileStraightforward synthesis of PET tracer precursors used for the early diagnosis of Alzheimers disease through Suzuki-Miyaura cross-coupling reactions, SDS of cas: 92-36-4, the publication is Tetrahedron (2013), 69(35), 7345-7353, database is CAplus.

In positron emission tomog. [¹¹C]PIB, Pittsburgh Compound-B, is currently the most widely used radiopharmaceutical for the early diagnosis of Alzheimer’s disease. Synthetic routes for the preparation of the precursor of [¹¹C]PIB are reported in the literature. These strategies require multiple steps and the use of protecting groups. This paper describes a simple 1-step synthesis of the precursor of [¹¹C]PIB through a Suzuki-Miyaura coupling reaction using thermal conditions or microwave activation. These methods were successfully applied to the synthesis of various 2-arylbenzothiazole and 2-pyridinylbenzothiazole compounds including [¹⁸F] precursor derivatives of PIB containing a nitro function.

Tetrahedron published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, SDS of cas: 92-36-4.

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

Taniguchi, Sayuri published the artcileInhibition of Heparin-induced Tau Filament Formation by Phenothiazines, Polyphenols, and Porphyrins, HPLC of Formula: 92-36-4, the publication is Journal of Biological Chemistry (2005), 280(9), 7614-7623, database is CAplus and MEDLINE.

Tau protein is the major component of the intraneuronal filamentous inclusions that constitute defining neuropathol. characteristics of Alzheimer’s disease and other tauopathies. The discovery of tau gene mutations in familial forms of frontotemporal dementia has established that dysfunction of the tau protein is sufficient to cause neurodegeneration and dementia. Here we have tested 42 compounds belonging to nine different chem. classes for their ability to inhibit heparin-induced assembly of tau into filaments in vitro. Several phenothiazines (methylene blue, azure A, azure B, and quinacrine mustard), polyphenols (myricetin, epicatechin 5-gallate, gossypetin, and 2,3,4,2′,4′-pentahydroxybenzophenone), and the porphyrin ferric deuteroporphyrin IX inhibited tau filament formation with IC₅₀ values in the low micromolar range as assessed by thioflavin S fluorescence, electron microscopy, and Sarkosyl insolubility Disassembly of tau filaments was observed in the presence of the porphyrin phthalocyanine. Compounds that inhibited tau filament assembly were also found to inhibit the formation of Aβ fibrils. Biochem. anal. revealed the formation of soluble oligomeric tau in the presence of the inhibitory compounds, suggesting that this may be the mechanism by which tau filament formation is inhibited. The compounds investigated did not affect the ability of tau to interact with microtubules. Identification of small mol. inhibitors of heparin-induced assembly of tau will form a starting point for the development of mechanism-based therapies for the tauopathies.

Journal of Biological Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H10N2O, HPLC of Formula: 92-36-4.

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