Tag: 200-300

Synthesis, characterization and evaluation of antibacterial and antifungal activity of 2-mercaptobenzothiazole and 2-mercaptobenzoxazole derivatives was written by Bhat, R.;Kumbhar, P.;Helavi, V.. And the article was included in Chemistry & Biology Interface in 2019.HPLC of Formula: 58759-63-0 This article mentions the following:

An efficient tandem route for unprecedented three component reaction involving 2-mercaptobenzoxazoles or 2-mercaptobenzothiazoles, salicylic acid and malononitrile was used for the development of new 2-mercapto-chromenopyridine derivatives I [R = H, 5-NO₂, 5-SO₃H; X = O, S]. The synthesized new derivatives I were characterized by various spectroscopic methods. In addition, compounds I were screened for in vitro antibacterial and antifungal activities against variety of bacterial and fungi strains resp. Some of the synthesized derivatives were existed to be potent antibacterial derivatives against S. aureus, E. coli, P. aeruginosa, B. subtilis, P. vulgaris and antifungal derivatives against C. coffeanum, A. niger, A. terreus and P. notatum. All these findings suggested that I [R = 5-NO₂, X = S; R = 5-SO₃H, X = O] might be further exploited as a new pharmacophore model for the development of anti-fungal agents. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0HPLC of Formula: 58759-63-0).

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

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

Relationship between structure and inhibiting action of derivatives of 2-aminothiazole was written by Voloshin, V. F.;Golosova, O. P.;Krasovskii, V. A.. And the article was included in Zashchita Metallov in 1986.Application of 6318-74-7 This article mentions the following:

The weight loss method was used to study the connection between the inhibiting action of derivatives of 2-aminothiazole and the nature of the substituent in its ring at their concentrations of 0.01M on steel St 3  [39296-41-8] in 10% solutions of HCl and H₂SO₄. At the same time, polarization measurements were made on Armco Fe samples pressed into Teflon as well as the impedance of the electrlyte/electrode interface at 25°. A correlation was observed between the pK_a value and the logarithm of the inhibition factor (γ) and the corrosion rate (K) in g/(m²-h). The following inhibitors were studied: 2-amino-4,5-diphenylthiazole; 2-amino-4-phenyl-5-tert-butylthiazole; 2-amino-5-methylbenzothiazole; 2-amino-4-methyl-5-isopropylthiazole; 2-amino-4-methylthiazole; 2-amino-4,5-dimethylthiazole; 2-aminothiazole; and 2-amino-4-methyl-5-acetylthiazole. The high electron d. on the heteroatom of the inhibitor mol. is important, but is not the only condition for protective activity of the compound In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application of 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. 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.Application of 6318-74-7

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

Decreased sulfotransferase SULT1C2 gene expression in DPT-induced polycystic kidney was written by Sugimura, Kazunobu;Tanaka, Tomoaki;Tanaka, Yoshihiko;Takano, Haruna;Kanagawa, Kenji;Sakamoto, Nobuyoshi;Ikemoto, Shin-Ichi;Kawashima, Hidenori;Nakatani, Tatsuya. And the article was included in Kidney International in 2002.Recommanded Product: 6318-74-7 This article mentions the following:

The pathogenesis of polycystic kidney disease (PKD) remains unclear despite the identification of the genes responsible for hereditary PKD. In this study, we investigated the alteration of gene expressions in an acquired PKD model induced by 2-amino-4,5-diphenylthiazole (DPT) using the differential display method. Kidney mRNA from a Sprague-Dawley rat fed with 1% DPT for 4 days and from a control rat was compared by the RT-PCR differential display method. Differentially expressed bands were re-amplified and subcloned. Using these subclones as probes, the changes in gene expressions were confirmed by Northern blot anal. Subsequently, mouse kidney cDNA library was screened. The isolated 1.5-kb cDNA contained an open reading frame encoding 296 amino acids, which shared 94.3% identity with rat SULT1C2 sulfotransferase, and was considered to be its mouse ortholog (GenBank Accession Number AY005469). Mouse SULT1C2 mRNA was abundant in the kidney and stomach among normal mouse tissues. The expression of SULT1C2 mRNA was decreased in the rat kidney after DPT feeding but not in the stomach. Mouse SULT1C2 was expressed successfully using pET plasmid vector and E. coli. The recombinant 34 kDa protein was capable of catalyzing the sulfation of p-nitrophenol at a K_m of 3.1 mmol/L, by utilizing 3′-phosphoadenosine 5′-phosphosulfate (PAPS) as the sulfate donor. Although the physiol. substrate and function of SULT1C2 have yet to be elucidated, its down-regulation could be involved in the cystic changes of tubules by decreasing the sulfation of the tubular basement membrane components. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Recommanded Product: 6318-74-7

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

Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide was written by Zeng, Weilan;Dang, Pan;Zhang, Xiaoyun;Liang, Yun;Peng, Caiyun. And the article was included in RSC Advances in 2014.Recommanded Product: 1843-21-6 This article mentions the following:

An efficient copper-catalyzed method for the synthesis of a variety of 2-aminobenzothiazoles was developed. The reaction proceeded from carbodiimide and sodium hydrosulfide via a tandem reaction in the presence of copper(II) trifluoromethanesulfonate affording the corresponding 2-aminobenzothiazole derivatives in good to perfect yields. 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. 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.Recommanded Product: 1843-21-6

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

β-Anilinovinyl derivatives of heterocyclic bases. III. Synthesis and absorption spectra of new anilinovinyl derivatives was written by van Dormael, A. E.;Nys, J.. And the article was included in Bulletin des Societes Chimiques Belges in 1952.Synthetic Route of C13H10N2S This article mentions the following:

Compounds of type I were prepared by refluxing 0.01 mole I (R = H, X = I) with 0.02 mole of the aniline with the desired substituent 10 min. in 25 ml. EtOH, adding 15 ml. concentrated HCl, and refluxing a further 2 hrs.; cooling, dilution with 75 ml. H₂O, filtering, and recrystallizing from alc. gave the following desired I [X^–, R, m.p. (crystallization solvent), λ_maximum (mμ), and log ε given]: I^–, CO₂H, 26-2° (EtOH), 423, 4.93; I^–, CO₂Et, 236-7° (EtOH), 425, 4.92; I^–, Ac, 220-1° (aqueous EtOH), 429, 4.80; Cl^–, NO₂, 200-1° (PrOH), 442, 4.56. The I were considered to be analogous to the monomethine cyanine (II) of the ethiodide of benzothiazole (C.A. 36, 467.1) and to the substituted anils (III) of PhNHCH:CHCHO. Since the III series could not be made, a number of the dianils (IV) of glutaconaldehyde, [R’C₆H₄NHCH:CHCH:CHCH:NHC₆H₄R’-p]⁺X^–, were prepared, the first 4 by the method of Zincke [via 1-(2,4-dinitrophenyl)pyridinium salts and ArNH₂], the last 3 by the method of König (via 1-cyanopyridinium bromide and ArNH₂) [R’, X, m.p., λ_maximum (mμ) given]: H, Cl, 165-7° (from Me₂CO by concentrated HCl, with repeated recrystallizations giving a lower m.p.), 485; Cl, Cl, 143° (MeOH), 494; MeO, Cl, 168-70° (3 EtOH crystallizations gave m. 127-9°), 509; Me₂N, Cl, 164-6°, 548; CO₂H, Cl, 177-9°, 498; CO₂Et, Br, 175-8°, 506; Ac, Br, 174-6°, 513; NO₂, Br, 149-50°, 524. λ_maximum for III were calculated on the assumption that they were 102.5 mμ less than for IV (C.A. 36, 467.1; 43, 1653⁺). An average of λ_maximum for II (423 mμ) and for III (calculated) was compared with λ_maximum for I exptl., with good agreement (neg. deviation contrary to expectation); results compared with similar ones for unsym. substituted trimethinic cyanines (C.A. 40, 5922.7). In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Synthetic Route of C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. 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.Synthetic Route of C13H10N2S

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

Synthesis of acid dyes derived from 2-aminothiazoles and their dyeing performance on wool and silk fabrics was written by Iyun, O. R. A.;Bello, K. A.;Jauro, A.. And the article was included in Journal of Chemical Society of Nigeria in 2012.Synthetic Route of C15H12N2S This article mentions the following:

Monoazo acid dyes based on 2-aminoheterocycles were prepared using J-, Nevile and Winther’s-, and H-acids with 4-sulfonic-phenyl-3-methyl-5-pyrazolone as the coupling components. The synthesized dyes were applied on wool and silk fabrics. The dyes were found to give a wide range of color shades with very good depth, brightness, and levelness. The visible absorption spectra and phys. properties of the dyes were also investigated. The percentage dyebath exhaustion on the fabrics was found to be excellent and the dyed fabrics showed very good fastness to light and washing. 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. 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. 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.Synthetic Route of C15H12N2S

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

Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions was written by Matviitsuk, Anastassia;Taylor, James E.;Cordes, David B.;Slawin, Alexandra M. Z.;Smith, Andrew D.. And the article was included in Chemistry – A European Journal in 2016.HPLC of Formula: 80945-86-4 This article mentions the following:

α,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topol. with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4HPLC of Formula: 80945-86-4).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.HPLC of Formula: 80945-86-4

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

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

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