Month: February 2023

Nitration of thiazoles and isothiazoles. Application to 2-benzyl- and 2-phenethylthiazoles and to their mono and dimethyl derivatives. Phenylthiazoles and -isothiazoles was written by Baule, Michel;Vivaldi, Robert;Poite, Jean C.;Dou, Henri J. M.;Vernin, Gaston;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1971.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

Nitration of a series of thiazoles and isothiazoles with concentrated HNO3-H2SO4 showed strong deactivation of the Ph group due to the effect of pos. pole of the thiazole or isothiazole ring, which behaved differently. The pos. pole oriented substitution meta and para in 2-benzylthiazoles and para in 2-phenethylthiazoles. The exptl. results and calculated theoretical electronic ds. were not in good agreement. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application In Synthesis of 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of 5-Phenylthiazole

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

Indolyl and dihydroindolyl N-glycinamides as potent and in vivo active NPY5 antagonists was written by Wu, Lingyun;Lu, Kai;Packiarajan, Mathivanan;Jubian, Vrej;Chandrasena, Gamini;Wolinsky, Toni C.;Walker, Mary W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Formula: C7H4ClNOS This article mentions the following:

A novel series of indolyl and dihydroindolyl glycinamides were identified as potent NPY5 antagonists with in vivo activity from screen hit I. The dihydroindolyl glycinamide II significantly inhibits NPY5 agonist induced feeding at a dose of 0.1 mg/kg. The indolyl glycinamide III also inhibits NPY5 agonist induced feeding at a dose of 1 mg/kg. Both II and III represent potential tools for further investigation into the biol. of the NPY5 receptor. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Formula: C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Formula: C7H4ClNOS

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

Action of chlorine on aryl thiocarbimides and the reactions of aryl isocyanodichlorides was written by Dyson, G. Malcolm;Harrington, Thomas. And the article was included in Journal of the Chemical Society in 1940.Recommanded Product: 1843-21-6 This article mentions the following:

PhNCS (20 g.) in 64 g. CHCl₃, treated with Cl without cooling until the increase in weight is 2 g., gives bis(phenylthiocarbimide) oxide, yellow, m. 118°; p-tolyl analog, m. 139°; m-isomer, m. 128°; p-bromophenyl analog; no oxides were obtained from o-MeC₆H₄NCS or from o-, m- and p-O₂NC₆H₄NCS. PhNCS (20 g.) in 10 g. CHCl₃, treated with Cl until the increase in weight is 7 g., gives 1-anilinobenzothiazole (I), m. 159° (picrate, yellow, m. 221°). CS(NHPh)₂ and Br in CHCl₃, boiled 0.5 h., give red needles of a Br addition product; reduction with SO₂ in H₂SO₃ and treatment with hot 2 N NaOH give I. PhNCS (318 g.) in 289 g. PhN:CCl₂ (II), treated with Cl with cooling for 8 h. (increase in weight of 363 g.) gives 256 g. of II, b. 209-11°, d¹⁵ 1.285; the following isocyanodichlorides were prepared by treatment with Cl in 2-3 times their weight of CS₂; they are colorless or pale yellow lachrymatory oils with unpleasant odors: p-bromophenyl, b₁₅ 122-4°, d¹⁵ 1.5; p-anisyl, b₁₅ 155-60°, d¹⁵ 1.5; p-tolyl, b₂₀ 121-4°, d¹⁵ 1.2; m-tolyl, b₁₀ 130°, d¹⁵ 1.35; o-tolyl, b₁₅ 125-30°, d¹⁵ 1.3; m-nitrophenyl, prepared in warm CHCl₃, pale yellow, b₁₅ 165-70°, m. 68°; m-isomer, m. 80°; the o-isomer could not be prepared II (5 g.) and 3.5 g. AcOH in 20 cc. C₆H₆, refluxed 2 h., give CO(NHPh)₂ (III); the o- and p-tolyl analogs were similarly obtained; however, boiling 10 g. II with 25 cc. AcOH in 50 cc. C₆H₆ for 10 h. gives PhNHAc (IV); o-, m- and p-MeC₆H₄NHAc were similarly prepared Thus the reaction with AcOH proceeds as follows: 2II + 3AcOH → III + CO₂ + HCl + 3AcCl; III + AcCl + AcOH → 2IV + CO₂ + HCl. III is only very slowly hydrolyzed to IV by AcOH alone whereas in the presence of AcCl the reaction is rapid and proceeds to completion. The m-tolyl analog yields an unidentified N compound m. 278°. p-BrC₆H₄N:CCl₂ and AcOH in C₆H₆ give (p-BrC₆H₄NH)₂CO on refluxing 5 h. and p-BrC₆H₄NHAc on further boiling; m-O₂NC₆H₄N:CCl₂ behaves similarly. II, PhNH₂ and C₆H₆, refluxed 5 h., give triphenylguanidine-HCl; analogs were prepared as follows, the m. p. of the HCl salt and the free base being given: phenyldi-p-tolyl 222-3°, 109°; m-isomer 206, 93°; o-isomer 205°, 100°; phenyldi-p-bromophenyl 257-62°, oil; p-tolyldiphenyl 230°, 128°; tri-p-tolyl 231°, 125°; p-tolyldi-p-bromophenyl 262-6°, 178°; tri-m-tolyl 221°, 107°; m-tolyldi-p-tolyl 218°, 105°; tri-o-tolyl 213-15°, 129°; o-tolyldi-p-tolyl 205-8°, 87°; tri-p-bromophenyl 270-6° (decomposition), 126°; p-bromophenyldi-p-tolyl 251°, 123°; m-nitrophenyldi-p-tolyl 201-5°, 179°; m-tolyl isomer 218-25°, 139°. The method constitutes a simple approach to the unsym. guanidines. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. 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.Recommanded Product: 1843-21-6

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

Development and characterization of 3-(arylsulfamoyl)benzamides as potent and selective SIRT2 inhibitors was written by Khanfar, Mohammad A.;Quinti, Luisa;Wang, Hua;Choi, Soo Hyuk;Kazantsev, Aleksey G.;Silverman, Richard B.. And the article was included in European Journal of Medicinal Chemistry in 2014.Quality Control of Thiazol-2-ylmethanamine This article mentions the following:

Inhibitors of sirtuin-2 deacetylase (SIRT2) have been shown to be protective in various models of Huntington’s disease (HD) by decreasing polyglutamine aggregation, a hallmark of HD pathol. The present study was directed at optimizing the potency of SIRT2 inhibitors containing the neuroprotective sulfobenzoic acid scaffold and improving their pharmacol. To achieve that goal, 176 analogs were designed, synthesized, and tested in deacetylation assays against the activities of major human sirtuins SIRT1-3. This screen yielded 15 compounds with enhanced potency for SIRT2 inhibition and 11 compounds having SIRT2 inhibition equal to reference compound AK-1. The newly synthesized compounds also demonstrated higher SIRT2 selectivity over SIRT1 and SIRT3. These candidates were subjected to a dose-response bioactivity assay, measuring an increase in α-tubulin K40 acetylation in two neuronal cell lines, which yielded five compounds bioactive in both cell lines and eight compounds bioactive in at least one of the cell lines tested. These bioactive compounds were subsequently tested in a tertiary polyglutamine aggregation assay, which identified five inhibitors. ADME properties of the bioactive SIRT2 inhibitors (e.g., I) were assessed, which revealed a significant improvement of the pharmacol. properties of the new entities, reaching closer to the goal of a clin.-viable candidate. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Quality Control of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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.Quality Control of Thiazol-2-ylmethanamine

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

Photo-induced copper-catalyzed C-H chalcogenation of azoles at room temperature was written by Gandeepan, Parthasarathy;Mo, Jiayu;Ackermann, Lutz. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Reference of 1826-13-7 This article mentions the following:

Inexpensive copper catalysts enabled direct C-H chalcogenations at ambient temperature by means of photo-induced catalysis. The expedient copper catalysis set the stage for C-S and C-Se bond formation from readily accessible non-volatile elemental chalcogens. The photo-assisted copper catalysis manifold proved suitable for a wide range of substrates with good functional group tolerance and exhibited high catalytic efficacy even at a reaction temperature of 25°. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Reference of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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 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.Reference of 1826-13-7

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

Reactions of 2-(arylamino)benzothiazoles with methyl acrylate was written by Ambartsumova, R. F.. And the article was included in Chemistry of Heterocyclic Compounds (New York)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) in 2000.Application of 1843-21-6 This article mentions the following:

Addition of 2-(arylamino)benzothiazoles to the C:C bond of CH₂:CHCO₂Me gives a mixture of isomeric 2-(arylimino)-3-[2-(methoxycarbonyl)ethyl]benzothiazolines and 2-{aryl-[2-(methoxycarbonyl)ethyl]amino}benzothiazoles. Their thermal stability was studied. HPLC anal. was used to follow the dynamics of the accumulation of the compounds formed in the reaction mixtures In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Application of 1843-21-6

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

Polymer-Supported Tribromide as a New Solid Phase and Recyclable Catalyst for the Synthesis of 2-(N-Arylamino)benzothiazoles Under Solvent-Free Microwave Irradiation Conditions was written by Nahakpam, Lokendrajit;Chingakham, Brajakishor S.;Laitonjam, Warjeet S.. And the article was included in Journal of Heterocyclic Chemistry in 2015.Name: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

The solid-phase synthesis of 2-(N-arylamino)benzothiazoles I (R¹ = H, 4-CH₃, 5-CH₃, 4-OCH₃; R² = H, 2-CH₃, 4-Cl, etc.) was achieved by reacting substituted thioureas with polymer-supported tribromide in high yield under microwave irradiation The method has several advantages such as short reaction time, good yields, and environmentally benign procedure. The catalyst could be recovered conventionally and reused at least four times without loss of its activity. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Name: N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Name: N-Phenylbenzo[d]thiazol-2-amine

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

Product class 18: benzothiazoles and related compounds was written by Ulrich, H.. And the article was included in Science of Synthesis in 2002.Computed Properties of C7H4N2O2S2 This article mentions the following:

Methods for preparing benzothiazoles and related annulated thiazoles are reviewed. Preparative methods include ring-closure reactions, ring transformations, aromatization and synthesis by substituent modification. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Computed Properties of C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Computed Properties of C7H4N2O2S2

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

Matrix Metalloproteinase Inhibitors: A Structure Activity Study was written by Levy, Daniel E.;Lapierre, France;Liang, Weisheng;Ye, Wenqing;Lange, Christopher W.;Li, Xiaoyuan;Grobelny, Damian;Casabonne, Marie;Tyrrell, David;Holme, Kevin;Nadzan, Alex;Galardy, Richard E.. And the article was included in Journal of Medicinal Chemistry in 1998.Name: Thiazol-2-ylmethanamine This article mentions the following:

Modifications around the dipeptide-mimetic core of hydroxamic acid based matrix metalloproteinase inhibitors I [AA = L-Trp, D-Trp, L-Trp(Me), L-3-benzothienylalanine, L-1- and -2-naphthylalanine, L-3- and -8-quinolylalanine, L-4-phenylphenylalanine, L-Phe, L-3- and -4-pyridylalanine, L–tert-leucine, L-abrine; R⁶ = NHMe, NH(CH₂)₄Me, NHCH₂CH₂OH, NHCH₂CH₂NHCO₂CH₂Ph, cyclopropylamino, cyclopentylamino, (S)- and (R)-1-indanylamino, (1R,2S)- and (1S,2R)-2-hydroxy-1-indanylamino, (S)-NHCHMePh, NHCH₂Ph, piperonylamino, 2-, 3-, and 4-pyridylmethylamino, 2-(4-pyridyl)ethylamino, NHCH₂CH₂C₆H₄OH-4, 2-furanylmethylamino, 2-thiazolylmethylamino, 2-benzimidazolylamino, 3-(1-imidazolyl)propylamino, 3-(4-morpholinyl)propylamino; R² = H, OH; R³ = CH₂CHMe₂, Bu, n-hexyl, n-octyl, OCHMe₂, O(CH₂)₄Me] were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1′ and P3′ substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess potent zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R³ as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities. 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. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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.Name: Thiazol-2-ylmethanamine

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

Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles was written by Saha, Prasenjit;Ramana, Tamminana;Purkait, Nibadita;Ali, Ashif Md;Paul, Rajesh;Punniyamurthy, Tharmalingam. And the article was included in Journal of Organic Chemistry in 2009.Computed Properties of C13H10N2S This article mentions the following:

The synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles is described via intramol. cyclization of o-bromoaryl derivatives using copper(II) oxide nanoparticles in DMSO under air. E.g., cyclization of o-bromoaryl amidine I gave 95% benzimidazoles II. The procedure is exptl. simple, general, efficient, and free from addition of external chelating ligands. It is a heterogeneous process and the copper(II) oxide nanoparticles can be recovered and recycled without loss of activity. 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 rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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