Heterocyclic Building Blocks-Thiazole

Thepchuay, Yanisa published the artcilePaper-based colorimetric biosensor of blood alcohol with in-situ headspace separation of ethanol from whole blood, Synthetic Route of 30931-67-0, the publication is Analytica Chimica Acta (2020), 115-121, database is CAplus and MEDLINE.

This work presents a novel development that exploits the concept of in-situ gas-separation together with a specific enzymic colorimetric detection to produce a portable biosensor called “Blood Alc. Micro-pad” for direct quantitation of ethanol in whole blood. The thin square device (25 mm × 25 mm × 1.8 mm) comprises two layers of patterned filter paper held together with a double-sided mounting tape with an 8-mm circular hole (the headspace). In operation, the reagent is deposited on one layer and covered with sticky tape. Then 8μL of a blood sample is dispensed onto the opposite layer and covered with sticky tape. Diffusion of ethanol across the 1.6 mm narrow headspace permits selective detection of ethanol by the enzymic reagents deposited on the opposite layer. This reagent zone contains alc. oxidase, horseradish peroxidase and 2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, as the chromogenic reagent. The color intensity, measured from the recorded digital image, resulting from the enzymic assay of ethanol, correlates with the concentration of blood alc. The results obtained with spiked mice and sheep blood samples, using an external calibration in the range of 1-120 mg dL^-1ethanol, gave recoveries of 93.2-104.4% (n = 12). The “Blood Alc. Micro-pad” gave good precision with %RSD <1 (50 mg dL^-1 ethanol, n = 10) and limit of quantification (10SD of intercept/slope) of 11.56 mg dL^-1. The method was successfully validated against a headspace gas chromatog.-mass spectrometric method. It has good potential for development as a simple and convenient blood alc. sensor for on-site testing.

Analytica Chimica Acta 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 C11H15NOS, Synthetic Route of 30931-67-0.

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

Lee, Nathanael J. published the artcileHexa (ethylene glycol) derivative of benzothiazole aniline promotes dendritic spine formation through the RasGRF1-Ras dependent pathway, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Biochimica et Biophysica Acta, Molecular Basis of Disease (2016), 1862(2), 284-295, database is CAplus and MEDLINE.

The authors’ recent study demonstrated that an amyloid-β binding mol., BTA-EG4, increases dendritic spine number via Ras-mediated signaling. To potentially optimize the potency of the BTA compounds, the authors synthesized and evaluated an amyloid-β binding analog of BTA-EG4 with increased solubility in aqueous solution, BTA-EG6. The authors initially examined the effects of BTA-EG6 on dendritic spine formation and found that BTA-EG6-treated primary hippocampal neurons had significantly increased dendritic spine number compared to control treatment. In addition, BTA-EG6 significantly increased the surface level of AMPA receptors. Upon investigation into the mol. mechanism by which BTA-EG6 promotes dendritic spine formation, the authors found that BTA-EG6 may exert its effects on spinogenesis via RasGRF1-ERK signaling, with potential involvement of other spinogenesis-related proteins such as Cdc42 and CDK5. Taken together, the authors’ data suggest that BTA-EG6 boosts spine and synapse number, which may have a beneficial effect of enhancing neuronal and synaptic function in the normal healthy brain.

Biochimica et Biophysica Acta, Molecular Basis of Disease 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, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Chen, Chao published the artcileSynthesis and biological evaluation of thiazole derivatives as novel USP7 inhibitors, HPLC of Formula: 774230-95-4, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(4), 845-849, database is CAplus and MEDLINE.

Herpesvirus-associated Ubiquitin-Specific Protease (HAUSP, also called USP7) interacts with and stabilizes Mdm2, and represents one of the first examples that deubiquitinases oncogenic proteins. USP7 has been regarded as a potential drug target for cancer therapy. Inhibitors of USP7 have been recently shown to suppress tumor cell growth in vitro and in vivo. Based on leading USP7 inhibitors P5091 and P22077, we designed and synthesized a series of thiazole derivatives The results of in vitro assays showed that the thiazole compounds, e.g., I, exhibited low micromolar inhibition activity against both USP7 enzyme and cancer cell lines. The compounds induced cell death in a p53-dependent and p53-independent manner. Taken together, this study may provide thiazole compounds as a new class of USP7 inhibitors.

Bioorganic & Medicinal Chemistry Letters published new progress about 774230-95-4. 774230-95-4 belongs to thiazole, auxiliary class Thiazole,Chloride,Aldehyde, name is 5-Chlorothiazole-2-ethanone, and the molecular formula is C5H4ClNOS, HPLC of Formula: 774230-95-4.

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

Kuhnert-Brandstaetter, Maria published the artcileThermal analytical and infrared spectroscopic investigations on polymorphic organic compounds. V., Computed Properties of 92-36-4, the publication is Mikrochimica Acta (1989), 3(1-2), 125-36, database is CAplus.

All the polymorphic compounds described are enantiotropic, so that in four cases, order-disorder or rotational transformation can be deduced on the basis of the relationships between enthalpy of transformation and enthalpy of fusion. The following compounds are of this type: (±)-1-azabicyclo[2.2.2]octan-3-ol (4 modifications), 5-norbornene-2,3-dicarboxylic anhydride (3 modifications), (1R)-(-)-camphorquinone (3 modifications) and 2-bromoethylamine-HBr (3 modifications). For tris(acetylacetonato)aluminum(III) (3 modifications) and 2-(4-aminophenyl)-6-methylbenzothiazole (5 modifications), another type of transformation must be assumed.

Mikrochimica Acta 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, Computed Properties of 92-36-4.

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

Chow, Wing-Kin published the artcilePalladium-Catalyzed Borylation of Aryl Mesylates and Tosylates and Their Applications in One-Pot Sequential Suzuki-Miyaura Biaryl Synthesis, Computed Properties of 791614-90-9, the publication is Chemistry – A European Journal (2011), 17(25), 6913-6917, S6913/1-S6913/47, database is CAplus and MEDLINE.

Palladium-catalyzed borylation with the N-methyl-2-(2′-dicyclohexylphosphino-5′-methoxyphenyl)indole (MeO-CM-Phos) ligand of ten aryl tosylates and twelve aryl mesylates gave the corresponding pinacol aryl boronates in 63% to 97% yield. The reaction conditions are mild and provide excellent functional-group compatibility (e.g., CN, CHO, COOMe, ketone, NH₂, benzodioxole, quinolyl, benzothiazole or NH-indole). E.g., reaction of 3-cyanophenyl mesylate with bis(pinacolato)diboron afforded pinacol (3-benzonitrile) boronate in 97% yield. The Pd/MeO-CM-phos catalyst system allows one-pot sequential reactions in the preparation of unsym. biaryls. Four biaryls were prepared by one-pot two-step and one-pot three-step transformations of aryl tosylates and 3-cyanophenol, resp.

Chemistry – A European Journal published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, Computed Properties of 791614-90-9.

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

Adams, A. published the artcileThiazoles derived from chrysean and isochrysean, HPLC of Formula: 101012-16-2, the publication is Journal of the Chemical Society (1956), 1870-7, database is CAplus.

Throughout this abstract, R is the thiazole nucleus. A solution of 25 kg. NaCN in 57 l. H₂O and 1 l. aqueous NH₃ (d. 0.88) was circulated through a 5′ × 6″ Pyrex tower packed with 1” Raschig rings, and treated with 15-16 kg. H₂S over 6 hrs. The H₂O-washed product was dried at 100° and crystallized from a mixture of 25 l. H₂O, 3.15 l. HOAc and 100 g. C, giving 920 g. chrysean, 2,5-H₂NSCRNH₂ (I), m. 215-16° (after further crystallization from N HOAc). The mother liquor was adjusted to pH 6 with NH₃, concentrated, and the crude residue H₂O-washed, giving 20.7 g. isochrysean, 4,5-H₂NSCRNH₂ (II), m. 131-50°. Further treatment of the filtrates gave an addnl. 106.7 g. crude II. Passing a sample through an alumina column gave pure II, m. 155° (from EtOH). Treating 1 g. I in 4 cc. C₅H₅N with 0.55 g. AcCl at 0-5° gave 0.8 g. Ac derivative, m. 250° (decomposition) (yellow needles from 2N HOAc). Similarly, 2,5-NCRNH₂ (III) (cf. C.A. 38, 3628⁶) with BzCl gave the Bz derivative, m. 211-12° (from EtOH); this was hydrolyzed by boiling 3 hrs. with 20% aqueous NaOH and acidifying the cold solution, giving 2,5-HO₂CRNHBz, m. 159°. PhCl was slowly distilled during 1 hr. from a mixture of 1 g. III, 1.4 g. o-C₆H₄(CO)₂O (IV), and 20 cc. PhCl, fresh solvent being added as needed. The product was washed with PhCl and dried giving 5,2-o-HO₂CC₆H₄CONHRCN (V), m. 253° (pale yellow, from MeOH), also m. 210° (decomposition) when placed in a pre-heated bath. Boiling V 1 hr. with aqueous NaOH gave 5,2-o-HO₂CC₆H₄CONHRCO₂H (VI), m. 154° (decomposition) (from dilute aqueous HCl). Boiling 1 g. VI with 15 cc. HOAc for 1 hr. gave 0.5 g. 5-o-C₆H₄(CO)₂NR, m. 147° (from aqueous HOAc). Boiling 10 g. III and 16.5 g. powdered IV 6 hrs. in 150 cc. HOAc gave 18.4 g. 5,2-o-C₆H₄(CO)₂NRCN (VII), m. 255-6° (orange needles, from HOAc). A stirred suspension of 50 g. VII in 825 cc. dry CHCl₃ and 20 g. dry EtOH was saturated at 0-5° with dry HCl and kept at 0° for 5 days. The resulting precipitate and 2 l. H₂O were heated on a steam bath 1 hr., giving 5,2-o-C₆H₄(CO)₂NRCO₂Et (VIII), m. 171° (pale yellow needles, from naphtha, b. 80-100°, and EtOH alternately) and unchanged VII. Stirring 90 cc. 100% N₂H₄.H₂O into a suspension of 58 g. VIII in 850 cc. EtOH, filtering the solution, letting it stand overnight, removing the solid, dissolving it in 2N NaOH, acidifying the solution, removing the precipitate, neutralizing the filtrate and concentrating it, and combining the resulting solid with the solid obtained by concentrating the original reaction filtrate, gave a total of 20 g. 5,2-H₂NRCONHNH₂, m. 190° (from H₂O, then from EtOH). When only 2 moles of N₂H₄ were used instead of an excess, the product was 5,2-H₂NRCO₂Et, m. 118° (cream-colored needles, from H₂O). 5,2-o-C₆H₄(CO)₂NRCO₂Bu (IX), m. 167-9° (pale yellow needles, alternately from ligroine and EtOH) was prepared in 54% yield in the same manner as VIII and was converted to 5,2-H₂NRCO₂Bu, m. 81-2° (from 2N HOAc, 69% yield). Hydrolysis of 2,5-NCRNHAc with dry HCl in EtOH-CHCl₃ gave 2,5-EtO₂CRNHAc (X), m. 191-2° (from H₂O); similarly was prepared 2,5-MeO₂CRNHAc, m. 216-17° (82% yield). Heating X with 100% N₂H₄.H₂O in EtOH 15 min. at 100°, then letting the mixture stand overnight gave 2,5-H₂NHNOCRNHAc, m. 286° (decomposition) (from EtOH). Diazotizing III in the presence of freshly precipitated CuCl gave 2,5-NCRCl (XI), m. 50° (from naphtha, b. 60-80°), accompanied by 2,5-H₂NOCRCl (XII), m. 189-91° (from EtOH). XI was converted into XII, m. 193°, by hydrolysis with dry HCl in CHCl₃-EtOH. Boiling XI 1 hr. in 2N NaOH gave 2,5-HO₂CRCl (XIII), m. 111-12°, purified by dissolving the sample in 2N NaOH, clarifying with C, and repptg. the free acid with 2N HCl. Treatment of XIII with CH₂N₂ gave the Me ester, m. 53° (from naphtha, b. 40-60°), which upon treatment with N₂H₄.H₂O gave 2,5-H₂NHNOCRCl, m. 197° (from EtOH). Mixing 1 g. XI with 2 cc. N₂H₄.H₂O and letting the mixture stand 2 hrs. gave 1.12 g. 5,2-ClRC(:NH)NHNH₂, m. 148° (decomposition) (pale yellow needles from EtOH), resolidifying and remelting at about 220°. Refluxing 5,2-p-AcNHC₆H₄SO₂NHRCSNH₂ 1.25 hrs. with 2N NaOH gave 5,2-p-H₂NC₆H₄SO₂NHRCO₂H (XIV), m. 189° (decomposition) (yellow-white, from naphtha, b. 60-80°, and EtOH). XIV in boiling H₂O gave 5-p-H₂NC₆H₄SO₂NHR, which with cold, dry NaOMe in MeOH gave (5-p-H₂NC₆H₄SO₂NNaR).MeOH, decomposition by 200°. Reduction of 5,2-p-O₂NC₆H₄SO₂NHRCSNH₂ with ammoniacal FeSO₄ gave 5,2-p-H₂NC₆H₄SO₂NHRCSNH₂, m. 219-20° (golden needles, from HOAc). Isochrysean derivatives were prepared as follows: II with AcCl in dry C₅H₅N at 0-5° gave 4,5-H₂NSCRNHAc (XV), m. 208-10° (pale yellow needles, from 2N HOAc); XV was converted to 4,5-NCRNHAc (XVI), m. 202° (from N HOAc) either by boiling 0.75 hr. with aqueous Pb(OAc)₂, or by shaking XV overnight at room temperature with a concentrated aqueous solution of Pb(NO₃)₂ to which 10% aqueous NaOH had been added until the precipitate redissolved. Boiling XV 1.5 hrs. with 2N NaOH and acidifying the resulting solution at 0° with 2N HCl gave 1,6-dihydro-2-methyl-6-thiazolo[4′,5′:5,4]pyrimidine, m. 266° (yellow), soluble in aqueous NaHCO₃ but not in dilute acid. Warming an Me₂CO suspension of XVI 45 min. with 20% aqueous H₂O₂ and 2N Na₂CO₃, Me₂CO being added as required to prevent precipitation of solid, then letting the mixture stand 16 hrs., gave 4,5-H₂NOCRNHAc (XVII), m. 212-13° (from H₂O); ultraviolet absorption data are given. XVII was also prepared from 4,5-H₂NOCRNH₂ with AcCl in dry C₅H₅N at 0-5°. Refluxing 10 g. II, 12.5 g. VI and 150 cc. HOAc 2 hrs. and letting the mixture stand overnight gave 5,4-o-HO₂CC₆H₄CONHRCSNH₂ (XVIII), m. 243-4° (pale yellow needles, from HOAc); treatment of XVIII with alk. Pb(NO₃)₂ as described previously gave 5,4-o-HO₂CC₅H₄CONHRCN (XIX), m. 224° (decomposition), hydrolyzed by 2N NaOH to 5,4-o-HO₂CC₆H₄CONHRCONH₂, m. 203° (decomposition), a white powder, resolidifying to yellow rhombohedra, m. 345-50°. Boiling XIX 2 hrs. with Ac₂O gave 5,4-o-C₆H₄(CO)₂NRCN, m. 196° (from Ac₂O). A solution of 5,4-H₂NRCO₂Et in dry C₅H₅N was treated at 0° with p-AcNHC₆H₄SO₂Cl and the crude product hydrolyzed by boiling 2 hrs. with 2N NaOH, giving 5,4-p-H₂NC₆H₄SO₂NHRCO₂H, m. 184° (decomposition) on slow heating, but immediate decomposition in a bath at 160°; the compound was believed to be the hemihydrate.

Journal of the Chemical Society published new progress about 101012-16-2. 101012-16-2 belongs to thiazole, auxiliary class Thiazole,Chloride,Carboxylic acid, name is 5-Chlorothiazole-2-carboxylic acid, and the molecular formula is C4H2ClNO2S, HPLC of Formula: 101012-16-2.

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

Piechowiak, Tomasz published the artcileChanges in the activity of flavanone 3β-hydroxylase in blueberry fruit during storage in ozone-enriched atmosphere, Recommanded Product: Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Journal of the Science of Food and Agriculture (2022), 102(3), 1300-1304, database is CAplus and MEDLINE.

The present study aimed to determine whether the ozonation process affects the flavonoid biosynthesis in highbush blueberry (Vaccinum corymbosum L.) fruit. Flavanone 3β-hydroxylase (F3H) was used as a marker of the flavonoid biosynthesis pathway. The activity of F3H, the expression of gene encoding F3H and the antioxidant status in blueberries treated with ozone at a concentration of 15 ppm for 30 min, every 12 h of storage, and maintained at 4°C for 4 wk were investigated. The results showed that ozonation process increases the expression of the F3H gene after 1 wk of storage, which translates into a higher catalytic capacity of protein, as well as a higher content of flavonoids and total antioxidant potential of ozonated blueberries compared to non-ozonated fruits. The present study provides exptl. evidence indicating that ozone treatment in proposed process conditions pos. affects flavonoid metabolism in highbush blueberry fruit leading to the maintainance of the high quality of the fruit during storage.

Journal of the Science of Food and Agriculture 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, Recommanded Product: 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

Martvon, A. published the artcileIsothiocyanates. XXXIII. Synthesis and infrared spectra of benzothiazolyl isothiocyanates, COA of Formula: C14H12N2S, the publication is Chemicke Zvesti (1973), 27(3), 387-92, database is CAplus.

Isothiocyanates I (R = H, NCS, Me; R1 = H, NCS; R2 = H; R3 = 4-Me, 4-MeO, 4-halo, 2-Cl, 3- and 4-NCS; R2 = 3-Cl, R3 = 4-NCS) (12 compounds) were prepared in 30-61% yields by treating amines I (R = H, H2N, Me; R1 = H, H2N; R2 = Cl, R3 = 4-H2N) with CSCl2.

Chemicke Zvesti 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, COA of Formula: C14H12N2S.

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

Vernin, Gaston published the artcileSynthesis and physicochemical study of sulfides, sulfoxides and sulfones in the thiazole series, Recommanded Product: 2-(Methylthio)thiazole, the publication is Journal of Heterocyclic Chemistry (1978), 15(8), 1361-6, database is CAplus.

The alkylation of Δ⁴-thiazoline-2-thiones under phase transfer catalysis conditions gave the corresponding thio ethers, e.g., I, in good yields. The oxidation of 2-alkylthiazoles with m-ClC₆H₄C(O)OOH gave the corresponding sulfoxides or sulfones depending on exptl. conditions in yields of âˆ?0-90%. IR, ¹H NMR mass spectra, and chromatog. data are reported for most of the compounds studied.

Journal of Heterocyclic Chemistry 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 C4H6N2, Recommanded Product: 2-(Methylthio)thiazole.

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

Mor, Satbir published the artcileConvenient and efficient synthesis of novel 11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-11-ones derived from 2-bromo-(2/3-substituted phenyl)-1H-indene-1,3(2H)-diones, Product Details of C7H5ClN2S, the publication is RSC Advances (2019), 9(23), 12784-12792, database is CAplus and MEDLINE.

An unprecedented formation of 11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-11-ones I (R¹ = 2-Me, 2-MeO, 2-F, 3-F; R² = H, Me, OMe, Cl, Br) through a one-step reaction of differently substituted 2-aminobenzenethiols 2-H₂N-5-R²C₆H₄SH and 2-bromo-(2/3-substituted phenyl)-1H-indene-1,3(2H)-diones II in freshly dried ethanol under reflux conditions has been investigated. This unique transformation probably occurs through an initial nucleophilic substitution followed by ring opening and subsequent intramol. cyclization. The structures of all the synthesized benzo[1,4]thiazino isoindolinones I were established by FTIR, ¹H NMR, ¹³C NMR, HRMS, and X-ray crystallog. anal. This approach was found to be simple and convenient and provides several advantages such as substantial atom economy, short reaction time and operational simplicity.

RSC Advances 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