Day: February 22, 2023

Aminobenzothiazoles. III. Tautomerism and unsaturation of the aminothiazole system was written by Hunter, R. F.. And the article was included in Journal of the Chemical Society in 1926.Application of 40172-65-4 This article mentions the following:

1-Aminobenzothiazole (I) and MeI at 100° for 5 hrs. give 1-imino-2-methyl-1,2-dihydrobenzothiazole (II), m. 123°, whose constitution was established by its synthesis from the dibromide, orange-red, sinters and softens at 125° (prepared from PhNMeC(:S)NH₂ and Br in CHCl₃). There is also probably formed some 1-methylaminobenzothiazole (III), m. 138°, which was prepared from the tetrabromide (IV), scarlet, m. 65-7° (decomposition) (prepared from PhNHC(:S)NHMe and Br in CHCl₃). Ethylation of I gave the 2-Et derivative corresponding to II, pale yellow, m. 85°, likewise prepared from its tetrabromide, vermilion-orange, m. 160-1° (decomposition). Acetylation of I gives almost quant. the 1-Ac derivative, m. 186°, also obtained by the reduction of its tetrabromide, orange-red, m. 137-9°; the isomer could not be obtained pure. II in CHCl₃, treated with excess of 20% Br in CHCl₃, gives a tribromide, orange, becomes white without melting at 245°. IV, exposed to the air for 20 hrs., loses Br and forms the orange-yellow dibromide, sinters 136°, chars at 191°; it loses more Br on further exposure. IV in absolute EtOH, after dilution with H₂O and concentration, gives a mixture of Br- and Br₂-substitution products, which could not be separated 1-Imino-2-acetyl-1,2-dihydrobenzothiazole (V), m. 118-20°, results by the reduction with H₂SO₃ of the dibromide (VI), orange, m. 130-2° (from the labile form of PhNHC(:S)NH₂); a 2nd form, purplish red, sinters 160°, m. 173° (decomposition), which is very stable in air and is more slowly reduced by SO₂, was also isolated. The HBr salt, dark chocolate prisms, turns orange 178° and m. 180° (decomposition). Hydrolysis of V gives I. 1-Benzoylaminobenzothiazole tetrabromide, orange-yellow, becomes colorless and loses Br at about 185°; boiling in EtOH gives 5-bromo-1-benzoylaminobenzothiazole, m. 226°. I, diazotized and treated with β-C₁₀H₇OH, gives benzothiazole-1-azo-β-naphthol, deep purple-red, m. 146°; it dyes cotton a fugitive shade of yellow; reduction gives I. 1-Aminoazobenzothiazole, cream-white, m. 135°; HCl salt, yellow, m. 232° (decomposition). With NaOCl this gives a dark purple compound, m. 156-8°. EtNO₂ in EtOH gives ψ-aminobenzothiazole, pale yellow, m. about 127°, isolated as the HCl salt, ruby-red or deep orange, m. 239-40°. ψ-Amino-3-toluthiazole HCl salt, ruby-red, sinters 145°, changes color at 145°; the corresponding 5-derivative, red, sinters 130°, softens about 150°. These facts establish the mobility of I. 5-Bromo-1-amino-benzothiazole dibromide (VII), orange-red, softens 80-2°, from p-BrC₆H₄NHC(:S)NH₂ and Br in CHCl₃; H₂SO₃ and NH₃ convert it into the free thiazole, m. 211°. 1-Acetylaminobenzothiazole hexabromide, orange-red, turns yellow at 130°, loses Br at 140° and becomes colorless at about 160°; in EtOH it gives 5-bromo-1-acetylaminobenzothiazole, m. 223°. VI in EtOH gives 5-bromo-1-imino-2-acetyl-1,2-dihydrobenzothiazole, m. 199-200°. Hydrolysis of each of these gives 5-bromo-1-aminobenzothiazole. 1-Amino-3-methylbenzothiazole, m. 136°, results by reduction of the dibromide, orange, m. 110° (decomposition), which in turn is formed from o-MeC₆H₄NHC(:S)NH₂ and Br in CHCl₃; the latter is unstable and loses Br in the air; in EtOH it gives the HBr salt, turns yellow at 260°, chars about 290°, of bromo-1-amino-3-methylbenzothiazole, m. 212°. 1-Amino-5-methylbenzothiazole, m. 142°, is formed from the dibromide-HBr, orange-red, m. 134° (decomposition); with EtOH the latter yields a Br substitution product, m. 210°. 1-Amino-4-methylbenzothiazole, m. 145°, from the tetrabromide, orange-red, m. about 250° (decomposition) after undergoing a series of color changes. The 3,5-di-Me derivative, m. 116°; its tetrabromide, red, does not m. 250° and is very unstable, losing Br and becoming colorless on exposure to the air for 0.5 hr. 2-Amino-β-naphthothiazole, sinters 220°, m. 235-7°; tetrabromide, orange, does not m. 260°; the corresponding α-derivative, sinters 230°, m. 249-51°; tetrabromide, yellow, m. 165° (decomposes). I dibromide in nearly boiling H₂O gives VII. In the experiment, the researchers used many compounds, for example, Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4Application of 40172-65-4).

Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4) 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.Application of 40172-65-4

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

Spread of carbapenem-resistant Klebsiella pneumoniae clinical isolates producing NDM-type metallo-β-lactamase in Myanmar was written by Takei, Satomi;Lu, Yu Jie;Tohya, Mari;Watanabe, Shin;Misawa, Shigeki;Tabe, Yoko;Miida, Takashi;Mya, San;Tin, Htay Htay;Tada, Tatsuya;Kirikae, Teruo. And the article was included in Microbiology Spectrum in 2022.HPLC of Formula: 78110-38-0 This article mentions the following:

A total of 38 isolates of carbapenem-resistant Klebsiella pneumoniae harboring blaNDM were obtained during surveillance of 10 hospitals in Myanmar. Of these 38 isolates, 19 (50%) harbored genes encoding 16S rRNA methylases, such as armA or rmtB. The K. pneumoniae strains tested belonged to 17 sequence types (STs), including the high-risk clonal lineages ST101 and ST147. The ST101 and ST147 isolates carried IncFII plasmids harboring blaNDM-5 and IncFIB(pQil) plasmids harboring blaNDM-1, resp. These results indicate that IncFII plasmids harboring blaNDM-5 and IncFIB(pQil) plasmids harboring blaNDM-1 have been spreading in K. pneumoniae ST101 and ST147 isolates, resp., in Myanmar. In the experiment, the researchers used many compounds, for example, 2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0HPLC of Formula: 78110-38-0).

2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0) 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. 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: 78110-38-0

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

Identification and migration studies of photolytic decomposition products of UV-photoinitiators in food packaging was written by Scarsella, Joseph B.;Zhang, Nan;Hartman, Thomas G.. And the article was included in Molecules in 2019.Computed Properties of C4H5NOS This article mentions the following:

UV-curable inks, coatings, and adhesives are being increasingly used in food packaging systems. When exposed to UV energy, UV-photoinitiators (PI’s) present in the formulations produce free radicals which catalyze polymerization of monomers and pre-polymers into resins. In addition to photopolymerization, other free radical reactions occur in these systems resulting in the formation of chem. varied photolytic decomposition products, many of which are low mol. weight chem. species with high migration potential. This research conducted model experiments in which 24 commonly used PI’s were exposed to UV-energy at the typical upper limit of com. UV-printing press conditions. UV-irradiated PI’s were analyzed by gas chromatog.-mass spectrometry (GC-MS) and electrospray-mass spectrometry (ESI-MS) in order to identify photolytic decomposition products. Subsequently, migration studies of 258 UV-cure food packaging samples were conducted using GC-MS; PI’s and photolytic decomposition products were found in nearly all samples analyzed. One hundred-thirteen photolytic decomposition products were identified. Eighteen intact PI’s and 21 photolytic decomposition products were observed as migrants from the 258 samples analyzed, and these were evaluated for frequency of occurrence and migratory concentration range. The most commonly observed PI’s were 2-hydroxy-2-methylpropiophenone and benzophenone. The most commonly observed photolytic decomposition products were 2,4,6-trimethylbenzaldehyde and 1-phenyl-2-butanone. This compilation of PI photolytic decomposition data and associated migration data will aid industry in identifying and tracing non-intentionally added substances (NIAS) in food packaging materials. In the experiment, the researchers used many compounds, for example, 2-Methoxythiazole (cas: 14542-13-3Computed Properties of C4H5NOS).

2-Methoxythiazole (cas: 14542-13-3) 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. 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.Computed Properties of C4H5NOS

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

Copper-mediated [3 + 2] cycloaddition of trifluoroacetimidoyl chlorides and N-isocyanoiminotriphenylphosphorane for the synthesis of 3-trifluoromethyl-1,2,4-triazoles was written by Yang, Hefei;Lu, Shu-Ning;Song, Yufei;Chen, Zhengkai;Wu, Xiao-Feng. And the article was included in Organic Chemistry Frontiers in 2021.COA of Formula: C7H9NS This article mentions the following:

Herein, a facile and straightforward route to synthesize 3-trifluoromethyl-1,2,4-triazoles via copper-mediated [3 + 2] cycloaddition of trifluoroacetimidoyl chlorides and N-isocyanoiminotriphenylphosphorane (NIITP) has been described. Mo(CO)₆ is utilized as an effective promotor to activate NIITP. The transformation features readily accessible reagents, mild reaction conditions, a broad substrate scope and high efficiency, and could be reproducible on a 3 mmol scale. In the experiment, the researchers used many compounds, for example, 4-(Methylthio)aniline (cas: 104-96-1COA of Formula: C7H9NS).

4-(Methylthio)aniline (cas: 104-96-1) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.COA of Formula: C7H9NS

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

Aqua[(benzothiazol-2-ylsulfanyl)acetato-κO]bis(1,10-phenanthroline-κ²N,N’)cadmium(II) nitrate monohydrate was written by Bian, He Dong;Huang, Fu Ping;Yu, Qing;Liang, Hong. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2007.Reference of 6295-57-4 This article mentions the following:

Crystals of the title compound are triclinic, space group P1̅; Z = 2. The Cd atom is coordinated by four N atoms [Cd-N 2.376(3)-2.394(3) Å] and two O atoms [Cd-O 2.240(2)-2.274(3) Å] in a distorted octahedral geometry. The crystal structure exhibits intermol. O-H···O H bonds and π-π stacking interactions. In the experiment, the researchers used many compounds, for example, 2-(Benzo[d]thiazol-2-ylthio)acetic acid (cas: 6295-57-4Reference of 6295-57-4).

2-(Benzo[d]thiazol-2-ylthio)acetic acid (cas: 6295-57-4) 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.Reference of 6295-57-4

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

Chemical synthesis, molecular modeling and pharmacophore mapping of new pyrrole derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth was written by Joshi, Shrinivas D.;Kumar, S. R. Prem;Patil, Sonali;Vijayakumar, M.;Kulkarni, Venkatarao H.;Nadagouda, Mallikarjuna N.;Badiger, Aravind M.;Lherbet, Christian;Aminabhavi, Tejraj M.. And the article was included in Medicinal Chemistry Research in 2019.Safety of 2-Amino-4-(3-bromophenyl)thiazole This article mentions the following:

Abstract: Substituted phenylthiazolyl benzamide and pyrrolyl benzamide derivatives were developed using mol. hybridization technique to create novel lead antimycobacterial mols. used to fight against Mycobacteriumtuberculosis. The newly synthesized mols. have inhibited InhA, the enoyl-ACP reductase enzyme from the mycobacterial type II fatty acid biosynthetic pathway. Of these, compound 3b showed H-bonding interactions with Tyr158 and co-factor NAD⁺ that binds the active site of InhA. All the mols. were screened for in vitro antitubercular activity against M. tuberculosis H₃₇Rv, as well as some representative mols. as the inhibitors of InhA. Thirteen compounds exhibited good anti-TB activities (MIC = 1.6μg/mL), but only few representative mols. showed the moderate InhA enzyme inhibition activity. [Figure not available: see fulltext.]. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(3-bromophenyl)thiazole (cas: 105512-81-0Safety of 2-Amino-4-(3-bromophenyl)thiazole).

2-Amino-4-(3-bromophenyl)thiazole (cas: 105512-81-0) 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 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.Safety of 2-Amino-4-(3-bromophenyl)thiazole

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

Impact of Preferential π-Binding in Catalyst-Transfer Polycondensation of Thiazole Derivatives was written by Smith, Mitchell L.;Leone, Amanda K.;Zimmerman, Paul M.;McNeil, Anne J.. And the article was included in ACS Macro Letters in 2016.Name: Methyl 2-amino-5-bromothiazole-4-carboxylate This article mentions the following:

Polymerizing electron-deficient arenes in a controlled, chain-growth fashion remains a significant challenge despite a decade of research on catalyst-transfer polycondensation. The prevailing hypothesis is that the chain-growth mechanism stalls at a strongly associated metal-polymer π-complex, preventing catalyst turnover. To evaluate this hypothesis, we performed mechanistic studies using thiazole derivatives and identified approaches to improve their chain-growth polymerization These studies revealed a surprisingly high barrier for chain-walking toward the reactive C-X bond. In addition, a competitive pathway involving chain-transfer to monomer was identified. This pathway is facilitated by ancillary ligand dissociation and N-coordination to the incoming monomer. We found that this chain-transfer pathway can be attenuated by using a rigid ancillary ligand, leading to an improved polymerization Combined, these studies provide mechanistic insight into the challenges associated with electron-deficient monomers and ways to improve their living, chain-growth polymerization Our mechanistic studies also revealed an unexpected radical anion-mediated oligomerization in the absence of catalyst, and a surprising oxidative addition into the thiazole C-S bond in a model system. In the experiment, the researchers used many compounds, for example, Methyl 2-amino-5-bromothiazole-4-carboxylate (cas: 850429-60-6Name: Methyl 2-amino-5-bromothiazole-4-carboxylate).

Methyl 2-amino-5-bromothiazole-4-carboxylate (cas: 850429-60-6) 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.Name: Methyl 2-amino-5-bromothiazole-4-carboxylate

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

Synthesis and anti-inflammatory activity of 2-amino substituted benzothiazoles was written by Pattan, Shashikant R.;Pujar, V. D.;Dighe, Nachiket S.;Musmade, Deepak S.;Hiremath, S. N.;Shinde, H. V.;Laware, R. B.. And the article was included in Asian Journal of Research in Chemistry in 2010.HPLC of Formula: 89793-81-7 This article mentions the following:

New pyrazinyl-substituted 2-aminobenzothiazoles were prepared by multiple steps. The structures of the synthesized compounds were confirmed by m.p., TLC, IR, and H¹ NMR. All the compounds showed promising anti-inflammatory activity. In the experiment, the researchers used many compounds, for example, 7-Nitrobenzo[d]thiazol-2-amine (cas: 89793-81-7HPLC of Formula: 89793-81-7).

7-Nitrobenzo[d]thiazol-2-amine (cas: 89793-81-7) 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.HPLC of Formula: 89793-81-7

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

Solubility of several sulfanilamide compounds in water and in water-alcohol mixtures was written by Sapozhnikova, N. V.;Postovskii, I. Ya.. And the article was included in Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) in 1944.Reference of 127-76-4 This article mentions the following:

The solubilities in water of sulfanilamide, sulfaguanidine, sulfapyridine, sulfamethylthiazole, sulfathiazole, sulfamethyldiazine and their Ac derivatives were determined at 20-39°. N’-heterocyclic derivatives have poor water solubility Heats of solution range from 9500 to 10, 600 cal./mol. All compounds, except diacetylsulfanilamide have maximum solubility in EtOH-water mixtures of 67-76% EtOH. Solubilities in water up to 100° are given in graphical form. In the experiment, the researchers used many compounds, for example, N-(4-(N-(Thiazol-2-yl)sulfamoyl)phenyl)acetamide (cas: 127-76-4Reference of 127-76-4).

N-(4-(N-(Thiazol-2-yl)sulfamoyl)phenyl)acetamide (cas: 127-76-4) 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.Reference of 127-76-4

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

Aztreonam in combination with imipenem-relebactam against clinical and isogenic strains of serine and metallo-β-lactamase-producing enterobacterales was written by Biagi, Mark;Lee, Michelle;Wu, Tiffany;Shajee, Aisha;Patel, Shitalben;Deshpande, Lalitagauri M.;Mendes, Rodrigo E.;Wenzler, Eric. And the article was included in Diagnostic Microbiology and Infectious Disease in 2022.Product Details of 78110-38-0 This article mentions the following:

The objective of this study was to evaluate the in vitro activity of aztreonam plus imipenem-relebactam against clin. and isogenic strains of Escherichia coli and Klebsiella pneumoniae co-harboring NDM and > 1 serine β-lactamase.Thirteen isolates were included: 4 clin. E. coli, 4 clin. K. pneumoniae, and 5 isogenic E. coli. Drugs were tested in time-kill analyses alone, in dual β-lactam combinations, and in triple drug combinations against all strains.All isolates were resistant to imipenem and imipenem-relebactam, and 85% were aztreonam-resistant. Neither imipenem nor imipenem-relebactam was bactericidal alone while aztreonam was bactericidal against 54% of isolates. The combination of aztreonam+imipenem was bactericidal and synergistic against 7/13 and 10/13 isolates. The addition of relebactam to this combination resulted in synergy against all 11 aztreonam-resistant clin. isolates.Aztreonam plus imipenem-relebactam may be a viable treatment option for aztreonam-non-susceptible NDM and serine β-lactamase-producing E. coli and K. pneumoniae. In the experiment, the researchers used many compounds, for example, 2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0Product Details of 78110-38-0).

2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Product Details of 78110-38-0

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