Day: February 9, 2023

Reactions of new nitroethane derivatives; formation of new 1,5-benzothiazepines and benzothiazoles III was written by Bercin, Erdogan;Uysal-Gokce, Mehtap;Noyanalpan, Ningur. And the article was included in Journal of Faculty of Pharmacy of Gazi University in 1996.SDS of cas: 1843-21-6 This article mentions the following:

The reactions of [(aminophenyl)thio]phenylnitroethane derivatives, 2-NH₂C₆H₄SCH(CH₂NO₂)C₆H₄R (2; R = H, Me) with isothiocyanates and benzaldehydes were studied. The reaction of 2 with isothiocyanates, R¹NCS (R¹ = Ph, 4-ClC₆H₄) gave 2-anilinobenzothiazoles I. Depending on the reaction temperature, 2 reacted with benzaldehydes (4-R¹C₆H₄CHO, R¹ = H, Cl, OMe, OEt) to give either 2-phenylbenzothiazole derivative II or 1,5-benzothiazepines III (R = H, Me, R¹ = H). In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6SDS of cas: 1843-21-6).

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 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.SDS of cas: 1843-21-6

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

Nickel-Catalyzed C-H Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules was written by Yamamoto, Takuya;Muto, Kei;Komiyama, Masato;Canivet, Jerome;Yamaguchi, Jun-Ichiro;Itami, Ken-Ichiro. And the article was included in Chemistry – A European Journal in 2011.Category: thiazole This article mentions the following:

Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. It has been established that Ni(OAc)₂/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)₂/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, a new protocol was discovered for the present coupling using Mg(OtBu)₂ as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodol. has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

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

Combinatorial Approach to N-Substituted Amino-Cyclitol Libraries by Solution-Phase Parallel Synthesis and Preliminary Evaluation as Glucocerebrosidase Inhibitors was written by Serrano, Pedro;Casas, Josefina;Zucco, Martine;Emeric, Gilbert;Egido-Gabas, Meritxell;Llebaria, Amadeu;Delgado, Antonio. And the article was included in Journal of Combinatorial Chemistry in 2007.Related Products of 69812-29-9 This article mentions the following:

Libraries of N-substituted amino-cyclitol derivatives of the scyllo and racemic chiro series by means of parallel solution-phase methodol. with the help of robotic technol. are described. Chem. diversity has been introduced by reaction of selected scaffolds with a set of aldehydes, acyl chlorides, sulfonyl chlorides, chloroformates, and amines to afford the corresponding amines, amides, sulfonamides, carbamates and ureas, resp. The optimized methodol. has proven excellent, in terms of overall purity of the resulting libraries, for the production of amides. Sulfonamides and carbamates have been obtained in slightly lower purity, while amines afforded modest results. Selected library members have been evaluated as inhibitors of recombinant glucocerebrosidase with K_i values ranging in the low micromolar scale for the most active members. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Related Products of 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Related Products of 69812-29-9

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

Biologically active fused heterocycles from naturally occurring quinones-Part-II: synthesis of 3-substituted-9-hydroxy-10-undecyl-benzo[2′,3′,:4,5]thiazolo[2,3-b]benzimidazole-8,11-diones and their antimicrobial activity was written by Rani, T. Usha;Rao, M.S.;Reddy, V. M.. And the article was included in Indian Journal of Heterocyclic Chemistry in 1997.Application of 58759-63-0 This article mentions the following:

Title compounds were prepared by condensation of 2-mercaptobenzimidazoles with bromoembelin and then converted into their acetyl, reduced acetyl, phenazine and N-acetylphenazine derivatives The compounds have been characterized by their anal. and spectral properties. Some of these compounds exhibit moderate antimicrobial activity. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Application of 58759-63-0).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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 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.Application of 58759-63-0

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

Syntheses of new sulfonamides. VIII. Syntheses of new hypoglycemic sulfonamides related to 2-sulfanilamido-5- isopropyl-1,3,4-thiadiazole was written by Takatori, Kichitaro;Yamada, Yasuo;Asano, Shingo. And the article was included in Yakugaku Zasshi in 1959.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

The following RSO₂Cl are prepared (R and m.p. given): p-AcNHC₆H₄, 149°; p-MeAcNC₆H₄, 126°; 3,4-Me(AcNH)C₆H₃, 159°; 4,3-Me(AcNH)C₆H₃, 142°; p-O₂NC₆H₄, 80°; Ph, 14.5°; p-MeC₆H₄, 69°; 3,6-Me₂C₆H₃, 24-6°; p-EtOCO₂C₆H₄, 71°, 6,2-EtOCO₂C₁₀H₆, 118°; p-FC₆H₄, 53°; p-BrC₆H₄, 76°; 2-acetamido-4-methyl-5-thiazolyl, 157° (decomposition). NH₂CSNHNH₂ (1 mole) and 2 moles corresponding acid chloride refluxed 1 hr., the product at 80-90° extracted with dilute HCl and made alk. with NH₄OH or Na₂CO₃ gave 2-amino-5-alkyl-1,3,4-thiadiazole (alkyl group and m.p. given): Me, 235°; Et, 196°; Pr, 203°; iso-Pr, 187°; Bu, 196°; iso-Bu, 229°; Am, 195°; undecyl, 115°. 2-Amino-5-isopropyl-1,3,4-thiadiazole (I) (0.1 mole) in 140 ml. C₅H₅N was heated 1 hr. at 100° with 0.1 mole p-AcNHC₆H₄SO₂Cl, the C₅H₅N removed and the residue treated with 100 ml. 10% HCl to give 28.4 g. 2-(p-AcNHC₆H₄SO₂NH) analog (II) of I, m. 183-4° (EtOH). II (28.4 g.) in 200 ml. 10% NaOH heated 1 hr. at 100° and the product recrystallized (H₂O) gave 15.4 g.2-(p-H₂NC₆H₄SO₂NH) analog of I, m. 195°. Similarly are prepared 2-RSO₂NH analogs of I (R and m.p. given): p-MeNHC₆H₄, 141°; 3,4-Me(H₂N)C₆H₃, 175°; 4,3-Me(H₂N)C₆H₃, 163°; p-HOC₆H₄, 100°; p-MeC₆H₄ (monohydrate), 93° (decomposition); 2,5-Me₂C₆H₃, 120°; p-O₂NC₆H₄, 172°; p-FC₆H₄, 97-9°; p-ClC₆H₄, 133°; p-BrC₆H₄, 142°; Ph, 125°; 2-acetamido-4-methyl-5-thiazolyl, 255-7° (decomposition). Condensation of equimolar amounts of 2-amino-5-alkyl-1,3,4-thiadiazole and p-MeC₆H₄SO₂Cl in C₅H₅N yielded 2-(p-toluenesulfonamido)-5-alkyl-1,3,4-thiadiazole (alkyl group and m.p. given): Me, 198°; Et, 130°; Pr, 139°; iso-Pr, 108°; Bu, 114°; Me₂CHCH₂, 175°; Am, 128°; Me(CH₂)₁₀, 92°. The sulfonamides of this series which have the power to reduce blood sugar level are generally soluble in dilute alk. carbonate, similar to N-acylated arenesulfonamides. This property was utilized for their purification. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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. 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 In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

The first potent inhibitors for human glutaminyl cyclase: synthesis and structure-activity relationship was written by Buchholz, Mirko;Heiser, Ulrich;Schilling, Stephan;Niestroj, Andre J.;Zunkel, Katrin;Demuth, Hans-Ulrich. And the article was included in Journal of Medicinal Chemistry in 2006.Computed Properties of C9H10N2O2S This article mentions the following:

The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the mols., which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Computed Properties of C9H10N2O2S).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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. 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.Computed Properties of C9H10N2O2S

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

Complexation of copper(II), cobalt(II), nickel(II) and chromium(III) with 2-hydroxy-, 2-hydrazo- and 2-phenylaminobenzothiazole in water-ethanol solutions was written by Manolov, S.;Davarski, K.;Auatai, I.. And the article was included in Koordinatsionnaya Khimiya in 1987.Safety of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Ligand acid dissociation and metal complexation constants were determined pH-metrically at 293 K in flowing N atm. Stability constants (log β) for 1:1 and 1:2 metal:ligand complexes decrease in the order Cr (III) > Cu(II) > Ni(II) ∼ Co(II). In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Safety of N-Phenylbenzo[d]thiazol-2-amine).

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. 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.Safety of N-Phenylbenzo[d]thiazol-2-amine

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

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