Month: January 2023

Transmission of substituent effects in heterocyclic systems by carbon-13 nuclear magnetic resonance. Benzothiazoles was written by Sawhney, Shanti N.;Boykin, David Withers. And the article was included in Journal of Organic Chemistry in 1979.Application of 68867-17-4 This article mentions the following:

The carbon-13 NMR spectra of 57 benzothiazoles, including 6-substituted 2-aminobenzothiazoles (I), 6-substituted 2-methylbenzothiazoles (II), 6-substituted benzothiazoles (III), 5-substituted 2-methylbenzothiazoles (IV), and 2-substituted benzothiazoles (V) were determined in (CD₃)₂SO. Single and dual parameter correlations of the chem. shifts with substituent constants were described for C-2 and C-9 of I, II, and III and for C-2 and C-3 of IV. Resonance effects are primarily responsible for the substituent effect on chem. shifts at these carbons. Transmission of substituent effects by the atom is limited, and the primary path of transmission to C-2 is through N. The data from series III and V suggest that transmission of substituent effects from C-2 to C-6 is ∼1/3 less effective than transmission from C-6 to C-2. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Application of 68867-17-4).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Application of 68867-17-4

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Similarities between catalase and cytosolic epoxide hydrolase was written by Guenthner, Thomas M.;Qato, Mazen;Whalen, Robert;Glomb, Sallie. And the article was included in Drug Metabolism Reviews in 1989.Synthetic Route of C15H12N2S This article mentions the following:

Cytosolic epoxide hydrolase, measured as trans-stilbene oxide hydrolase activity, was isolated and purified from human and guinea pig liver cytosol. Antiserum to the guinea pig liver preparation reacted strongly with bovine liver catalase. This lack of selectivity of the antiserum was due to catalase contamination of the epoxide hydrolase preparation It was also determined that several com. catalase preparations are contaminated with cytosolic epoxide hydrolase. The human epoxide hydrolase preparation used here contained no detectable catalase contamination, yet antiserum to this protein also cross-reacted slightly with catalase, indicating some intrinsic similarity between the 2 enzymes. It is concluded that catalase and cytosolic epoxide hydrolase contain some similar immunogenic epitopes, and it is surmised that similarities between the subunits of these 2 enzymes may lead to their partial copurifn. Functional similarities between the 2 enzymes are also demonstrated, as several compounds that inhibit catalase also inhibit cytosolic epoxide hydrolase activity in the same concentration range and rank order. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Synthetic Route of C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Synthetic Route of C15H12N2S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Thermal analyses and spectral characterization of some synthesized metal(II) Schiff base complexes was written by Jain, Rajendra K.;Mishra, A. P.;Gupta, Priya. And the article was included in Journal of Thermal Analysis and Calorimetry in 2012.Category: thiazole This article mentions the following:

Schiff base metal complexes derived from 2-thiophenecarboxylidine-4-anisidine, 3,4-dihydroxy-5-nitrobenzylidine-2-amino-5-methylthiazole and 3,4-dihydroxy-5-nitrobenzylidine-4-chloroaniline were synthesized and characterized by elemental anal., IR, UV-visible, molar conductance and thermal analyses. The complexes are colored and stable in air at room temperature The complexes exhibit coordination number to be 4 and 6. The thermal behavior of metal complexes shows that the hydrated complexes lose water mols. of hydration in the first and then is immediately followed by decomposition of ligand mols. in the subsequent steps. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Category: thiazole).

2-Methylthiazol-5-amine (cas: 89281-44-7) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Influence of steric factors on the interaction of isomeric phenyloxazoles and phenylthiazoles with microsomal oxidation was written by Smith, Leverett R.;Wilkinson, Christopher F.. And the article was included in Biochemical Pharmacology in 1978.Recommanded Product: 5-Phenylthiazole This article mentions the following:

5-Phenyloxazole (I) [1006-68-4] and 5-phenylthiazole (II) [1826-13-7] showed a high inhibitory activity and low spectral (type II) dissociation (K_s) towards both rat liver microsomal and armyworm midgut preparations 4-Phenyloxazole [20662-89-9] had a high K_s, and 2-phenyloxazole [20662-88-8], 4-phenylthiazole [1826-12-6], 2-phenylthiazole (III) [1826-11-5], benzoxazole [273-53-0], and benzothiazole [95-16-9] showed little spectral interactions with microsomes; none other than III had any significant inhibitory effects. The lack of type II binding by III suggests that its mode of action differs from that of I and II. The results are consistent with the steric model developed previously with the imidazoles. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Recommanded Product: 5-Phenylthiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Discovery of Piperazin-1-ylpyridazine-Based Potent and Selective Stearoyl-CoA Desaturase-1 Inhibitors for the Treatment of Obesity and Metabolic Syndrome was written by Zhang, Zaihui;Sun, Shaoyi;Kodumuru, Vishnumurthy;Hou, Duanjie;Liu, Shifeng;Chakka, Nagasree;Sviridov, Serguei;Chowdhury, Sultan;McLaren, David G.;Ratkay, Leslie G.;Khakh, Kuldip;Cheng, Xing;Gschwend, Heinz W.;Kamboj, Rajender;Fu, Jianmin;Winther, Michael D.. And the article was included in Journal of Medicinal Chemistry in 2013.Name: Thiazol-2-ylmethanamine This article mentions the following:

Stearoyl-CoA desaturase-1 (SCD1) catalyzes de novo synthesis of monounsaturated fatty acids from saturated fatty acids. Studies have demonstrated that rodents lacking a functional SCD1 gene have an improved metabolic profile, including reduced weight gain, lower triglycerides, and improved insulin response. In this study, we discovered a series of piperazinylpyridazine-based highly potent, selective, and orally bioavailable compounds Particularly, compound I (XEN103) was highly active in vitro (mSCD1 IC₅₀ = 14 nM and HepG2 IC₅₀ = 12 nM) and efficacious in vivo (ED₅₀ = 0.8 mg/kg). It also demonstrated striking reduction of weight gain in a rodent model. Our findings with small-mol. SCD1 inhibitors confirm the importance of this target in metabolic regulation, describe novel models for assessing SCD1 inhibitors for efficacy and tolerability and demonstrate an opportunity to develop a novel therapy for metabolic disease. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Name: Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Name: Thiazol-2-ylmethanamine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

2-Amino-4(or 5)-arylthiazoles. I. Ultraviolet absorption spectra of alkyl- or phenyl-substituted compounds was written by Okamiya, Jiro. And the article was included in Nippon Kagaku Zasshi in 1959.SDS of cas: 6318-74-7 This article mentions the following:

Ultraviolet absorption spectra were reported for 2-aminothiazole, 2-amino-4-methylthiazole, 2-amino-5-methylthiazole, 2-amino-4-ethyl-5-methylthiazole, 2-amino-4,5-tetramethylenethiazole, 2-amino-4,5-benzothiazole, 2-amino-4-phenylthiazole, 2-amino-5-phenyl-5-methylthiazole, 2-amino-4-(p-tolyl)thiazole, 2-amino-4-(o-tolyl)thiazole, 2-amino-4-(o-tolyl)-5-methylthiazole, m. 124°, 2-amino-4-mesitylthiazole, m. 169°, 2-amino-4-mesityl-5-methylthiazole, m. 123-4°, 2-amino-5-phenylthiazole, 2-amino-4-methyl-5-phenylthiazole, m. 171°, 2-amino-4,5-diphenylthiazole, 2-amino-4-(p-tolyl)-5-phenylthiazole, m. 179°, 2-amino-4-phenyl-5-(p-tolyl)thiazole, m. 176°, 2-amino-4,5-bis(p-tolyl)thiazole, m. 167°, 2-amino-4,5-dihydronaphtho[1,2]thiazole, 4,4′-bis(2-amino-4-thiazolyl)bibenzyl, m. 230-45° (decomposition), 2,2′-diamino-4,4′-diphenyl-5,5′-bithiazolyl (I), 1,2-bis(2-amino-4-phenyl-5-thiazolyl)ethane, m. 238°, 1,5-bis(2-amino-4-phenyl-5-thiazolyl)pentane (II), m. 165°, and 1,6-bis(2-amino-4-phenyl-5-thiazolyl)hexane. Spectra of alkyl derivative were almost the same. Spectra of 4-phenyl compounds had maximum at longer wave lengths than those of 4-phenyl-5-alkyl compounds, indicating the presence of steric hindrance. II had twice the intensity of other thiazoles, while I was weaker because of steric effects. The 5-phenyl compounds had maximum at longer wave lengths than the 4-phenyl compounds 4,5-Diaryl compounds seemed to have a fair amount of resonance (from the spectra), in spite of the expected steric hindrance. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7SDS of cas: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.SDS of cas: 6318-74-7

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Sequencing Groebke-Blackburn-Bienayme and Aza-Michael Addition Reactions: A Modular Strategy for Accessing a Diverse Collection of Constrained Benzoxazepine and Imidazopyrazine Systems was written by Srinivasulu, Vunnam;Al-Marzooq, Farah;Hamad, Mohamad;Khanfar, Monther A.;Ramanathan, Mani;Soares, Nelson C.;Al-Tel, Taleb H.. And the article was included in Synthesis in 2021.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

A divergent strategy that permitted the access to diversely functionalized benzoxazepinium scaffolds fused to various heterocycles was reported. The described strategy featured a one-pot combination of the Groebke-Blackburn-Bienaym reaction and an aza-Michael addition Me (E)-4-(2-formylphenoxy)but-2-enoates were utilized as central elements in this cascade. These building blocks were reacted with a variety of functionalized amino-azines and tert-Bu isocyanide under ytterbium triflate [Yb(OTf)₃] catalysis. The cascade represented a rapid, modular and atom-economic process that leaded to the construction of a diverse collection of constrained benzoxazepinium systems from a wide substrate scope. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application In Synthesis of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Application In Synthesis of 4,5-Diphenylthiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

An approach to the synthesis of 4-phenyl-5-(arylimino)-Δ²-1,2,3,4-thiatriazolines was written by L’Abbe, Gerrit;Franek, Walter;Toppet, Suzanne;Delbeke, Pieter. And the article was included in Journal of Heterocyclic Chemistry in 1990.Reference of 1843-21-6 This article mentions the following:

4-Phenyl-5-arylimino-Δ²-1,2,3,4-thiatriazolines I (R = Ph, 4-MeC₆H₅) are presumably formed by reacting 5-arylaminothiatriazoles II with benzene at 50°, but decompose in situ to benzothiazole derivatives III. The reaction mechanism is discussed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Reference of 1843-21-6

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Structure of phenyl isothiocyanate and methyl isothiocyanate sulfides was written by Paranjpe, M. G.. And the article was included in Indian Journal of Chemistry in 1968.Computed Properties of C13H10N2S This article mentions the following:

“Phenyl isothiocyanate sulfides” (I) or “methyl isothiocyanate sulfide” (II) gave the tabulated RNHCSNHR1 (III) when treated with R1NH2 in “sulfide”-amine ratios 1:>2. Reaction of I or II with R1NH2 in ratios 1:<1 90-120 min. gave, resp., R1NHCSNPhCSNHPh (IV) or R1NHCSNMeCSNHMe (V) as well as III. Refluxing CHCl3 was used with I; with II the reaction temperature was 100°, but no solvent was used (reactant “sulfide”, R1, R, m.p. of IV or V, and m.p. of III given): I, PhCH2, Ph, 129°, 148; I, cyclohexyl, Ph, 135°, 149°; I, Bu, Ph, 145°, 68°; I, sec-Bu, -, 140°, -; II, PhCH2, PhCH2, 109°, 149° [also obtained was III (R = Me), m. 78°]; II, cyclohexyl, cyclohexyl, 138°, 179°. [TABLE OMITTED] On warming IV (R1 = PhCH2) (VI) with Na plumbite solution desulfurization was observed. Boiling VI with aqueous MeNH2 afforded III (R = Ph, R1 = Me) and III (R = Ph, R1 = PhCH2). VI (1 g.), 0.8 ml. PhCH2Cl, and 20 ml. EtOH, refluxed 5 hrs. gave the 3-benzyl analog, m. 154° (EtOH), which with alc. NH4OH decomposed into III (R = Ph, R1 = PhCH2). VI (2 g.) in 40 ml. dry CHCl3, treated with Br in CHCl3 until color persisted, yielded a hydrobromide, m. 228°, which on basification yielded the free base, 2-phenylaminobenzothiazole, m.p. and mixed m.p. 158°. Thus the identity of VI was determined A mixture of 8 g. 1,3-dimethylthiourea, 8 ml. PhCH2Cl, and 50 ml. EtOH was refluxed 90 min., cooled, basified (NH4OH), and extracted with C6H6. The dried extract was kept overnight with 8 ml. CS2 and treated with 12 g. Br in 40 ml. C6H6 to give a hydrobromide, m. 236°, which on NH4OH basification gave 3.8 g. 4-methyl-5-methylimino-1,2,4-dithiazolidine-3-thione (II), m. 86° (identical with an authentic sample), which on warming with EtOH yielded the isomer (VII), m.p. and mixed m.p. 120° (Freund, 1904, 1895). Ir spectra of I and II are reported. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Computed Properties of C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Computed Properties of C13H10N2S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

One pot synthesis using supported reagents system KSCN/SiO₂-RNH₃OAc/Al₂O₃: synthesis of 2-aminothiazoles and N-allylthioureas was written by Aoyama, Tadashi;Murata, Sumiko;Arai, Izumi;Araki, Natsumi;Takido, Toshio;Suzuki, Yoshitada;Kodomari, Mitsuo. And the article was included in Tetrahedron in 2006.Quality Control of 4,5-Diphenylthiazol-2-amine This article mentions the following:

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles and N-allylthioureas from com. available materials in one pot by using a supported reagents system, KSCN/SiO₂-RNH₃OAc/Al₂O₃, in which α-halo ketones react first with KSCN/SiO₂ and the product, α-thiocyanatoketone, reacts with RNH₃OAc/Al₂O₃ to give the final products, 2-aminothiazoles, in good yield. Allyl bromides react with KSCN/SiO₂ and the products, allyl isothiocyanates, react with RNH₃OAc/Al₂O₃ to give N-allylthioureas. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Quality Control of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Quality Control of 4,5-Diphenylthiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica