Month: February 2023

The opposite and amplifying effect of B ← N coordination on photophysical properties of regioisomers with an unsymmetrical backbone was written by Zeng, Chao;Yuan, Kang;Wang, Nan;Peng, Tai;Wu, Gang;Wang, Suning. And the article was included in Chemical Science in 2019.Name: 2-Bromothiazole This article mentions the following:

1,3-Dipolar cycloaddition of pyrido[2,1-a]isoindole with internal alkynes functionalized by a BMes₂ph and an N-aromatic heterocycle leads to the formation of two types of regioisomers (major a and minor b) that have distinct phys. and photophys. properties. Examination on 5 pairs of regioisomers unveils that the major isomers consistently have a smaller optical energy gap and emission energy than the corresponding minor isomers, which is greatly amplified by the formation of an internal B ← N bond. The regioisomers with a B ← N bond display contrasting temperature-dependent structural dynamics and response to fluoride ions, owing to an entropy-driven or fluoride initiated B ← N bond rupture/ring-opening process and the different B ← N bond strength. The opposite inductive effect and the Lewis pair properties of the dichotomic substituent units are responsible for the contrasting properties of the regioisomers in this system. In the experiment, the researchers used many compounds, for example, 2-Bromothiazole (cas: 3034-53-5Name: 2-Bromothiazole).

2-Bromothiazole (cas: 3034-53-5) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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: 2-Bromothiazole

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

Synthesis of the (benzothiazolylthio)carboxylic acids by use of ultrasound irradiation in phase transfer catalysis medium was written by Li, Yingjun;Li, Lina;Sun, Shuqin;Hu, Zhijun;Song, Yongbo. And the article was included in Hebei Shifan Daxue Xuebao, Ziran Kexueban in 2011.Synthetic Route of C9H7NO2S2 This article mentions the following:

(Benzothiazolylthio)carboxylic acids, (2-benzothiazolylthio)acetic acid and 3-(2-benzothiazolylthio)propionic acid were synthesized by the technique of ultrasonic irradiation and phase transfer catalysis. Their structures were confirmed by IR, ¹HNMR and ¹³CNMR. The influences of the reaction temperature, the reaction time, the solvent, the catalyst and the ultrasonic irradiation on the reaction were investigated and optimum exptl. conditions were found. Compared with the literature methods, this synthetic method had such advantages as mild condition, simple operation, short reaction time, lower reaction temperature and higher yield. In the experiment, the researchers used many compounds, for example, 2-(Benzo[d]thiazol-2-ylthio)acetic acid (cas: 6295-57-4Synthetic Route of C9H7NO2S2).

2-(Benzo[d]thiazol-2-ylthio)acetic acid (cas: 6295-57-4) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Synthetic Route of C9H7NO2S2

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

Catalyst and additive-free regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with elemental sulfur/selenium and TMSCN was written by Feng, Chengtao;Peng, Ya;Ding, Guangrong;Li, Xiangxiao;Cui, Chang;Yan, Yizhe. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.Recommanded Product: 15864-32-1 This article mentions the following:

A regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with TMSCN and elemental sulfur/selenium was demonstrated under catalyst-free and additive-free conditions. DMSO (DMSO) was employed as the mild oxidant as well as the solvent. The reaction was operationally simple and scalable with a broad substrate scope. Compared to previous reports, this protocol was distinguished by avoiding the use of any catalyst or additive, the novel SCN/SeCN source, the different reaction mechanism and gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 2-Amino-6-bromobenzothiazole (cas: 15864-32-1Recommanded Product: 15864-32-1).

2-Amino-6-bromobenzothiazole (cas: 15864-32-1) 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.Recommanded Product: 15864-32-1

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

A pharmacologic activator of endothelial KCa channels increases systemic conductance and reduces arterial pressure in an anesthetized pig model was written by Mishra, Ramesh C.;Mitchell, Jamie R.;Gibbons-Kroeker, Carol;Wulff, Heike;Belenkie, Israel;Tyberg, John V.;Braun, Andrew P.. And the article was included in Vascular Pharmacology in 2016.Safety of Naphtho[1,2-d]thiazol-2-amine This article mentions the following:

SKA-31, an activator of endothelial KCa2.3 and KCa3.1 channels, reduces systemic blood pressure in mice and dogs, however, its effects in larger mammals are not well known. We therefore examined the hemodynamic effects of SKA-31, along with sodium nitroprusside (SNP), in anesthetized, juvenile male domestic pigs. Exptl., continuous measurements of left ventricular (LV), aortic and inferior vena cava (IVC) pressures, along with flows in the ascending aorta, carotid artery, left anterior descending coronary artery and renal artery, were performed during acute administration of SKA-31 (0.1, 0.3, 1.0, 3.0 and 5.0 mg/mL/kg) and a single dose of SNP (5.0 μg/mL/kg). SKA-31 dose-dependently reduced mean aortic pressure (mP_AO), with the highest dose decreasing mP_AO to a similar extent as SNP (- 23 ± 3 and – 28 ± 4 mm Hg, resp.). IVC pressure did not change. Systemic conductance and conductance in coronary and carotid arteries increased in response to SKA-31 and SNP, but renal artery conductance was unaffected. There was no change in either LV stroke volume (SV) or heart rate (vs. the preceding control) for any infusion. With no change in SV, drug-evoked decreases in LV stroke work (SW) were attributed to reductions in mP_AO (SW vs. mP_AO, r² = 0.82, P < 0.001). In summary, SKA-31 dose-dependently reduced mP_AO by increasing systemic and arterial conductances. Primary reductions in mP_AO by SKA-31 largely account for associated decreases in SW, implying that SKA-31 does not directly impair cardiac contractility. In the experiment, the researchers used many compounds, for example, Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4Safety of Naphtho[1,2-d]thiazol-2-amine).

Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Safety of Naphtho[1,2-d]thiazol-2-amine

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

Synthesis and Antimicrobial Activity of Aurone Derivatives Containing Heterocyclic Substituents was written by Li, Yi;Zhao, Haiqing;Niu, Chao;Aisa, Haji Akber;Hou, Xueling. And the article was included in Russian Journal of General Chemistry in 2022.Product Details of 3364-80-5 This article mentions the following:

A series of aurone compounds with the B ring substituted by different heterocycles has been synthesized. All synthesized compounds have been tested for antibacterial activity. It has been determined that different heterocyclic substituents modulate the antibacterial spectrum of aurones. Indole-substituted aurones display good inhibitory activity against Gram-pos. bacteria. Thiophene-substituted aurones exhibit inhibitory activity against fungi. Aminopyrimidine-substituted aurones exhibit promising inhibitory activity against Gram-neg. bacteria. Authors have determined that 2-arylimidazo[1,2-a]pyridones I (R¹ = H, OMe) can be used as a platform for antifungal agents design. In the experiment, the researchers used many compounds, for example, Thiazole-4-carbaldehyde (cas: 3364-80-5Product Details of 3364-80-5).

Thiazole-4-carbaldehyde (cas: 3364-80-5) 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.Product Details of 3364-80-5

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

Neuromodulatory potential of Asparagus racemosus and its bioactive molecule Shatavarin IV by enhancing synaptic acetylcholine level and nAChR activity was written by Shuchi Smita, Shachi;Trivedi, Mashu;Tripathi, Deepika;Pandey-Rai, Shashi;Pandey, Rakesh. And the article was included in Neuroscience Letters in 2021.COA of Formula: C11H12N2S This article mentions the following:

Cholinergic dysfunction has been commonly known to be associated with plethora of neurodegenerative disorders and also serves as a biomarker. Recently, cholinergic system demonstrated that acetylcholine has major role in regulation of its function therefore the main therapeutic regimens towards disease management have been focused on increasing acetylcholine levels. The current study explores the potential of Asparagus racemosus extract (ARE) and its bioactive mol. Shatavarin IV (SIV) in improving cholinergic transmission via utilizing Caenorhabditis elegans considering as a model system. Observations and results obtained through this study have clearly showed significant modulation in cholinergic function by increasing acetylcholine (ACh) levels and the nicotinic acetylcholine receptors (nAChRs) activity. Further exploration on mechanistic facet pointed towards ARE and SIV modulatory potential through increased synaptic ACh level by blocking acetyl cholinesterase at enzyme level and by regulating increment in transcript level of cha-1, and cho-1 that are directly responsible for the synthesis of ACh. Further, the up-regulation of unc-38 and unc-50 transcripts could be the reason for enhanced nAChR activity and investigation on stress modulator activity showed excellent efficiency of ARE and SIV in diminishing ROS thereby lowering the oxidative damage. In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4COA of Formula: C11H12N2S).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.COA of Formula: C11H12N2S

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

Crystalline vitamin B₁. XIII. Ultraviolet absorption of some derivatives of the basic cleavage product and their synthetic analogs was written by Ruehle, A. E.. And the article was included in Journal of the American Chemical Society in 1935.Recommanded Product: 20485-41-0 This article mentions the following:

The ultraviolet absorption of the basic cleavage product of vitamin B₁ is not only similar to that of the thiazoles but its derivatives exhibit absorption similar to that of corresponding thiazole derivatives Curves are given for the basic product, 4-methyl-, 2,4-dimethyl- and 2-hydroxy-4-methylthiazole HCl salts, 4-methylthiazole-EtI, 4-methylthiazole-5- carboxylic acid and the Cl derivative of the basic product. In the experiment, the researchers used many compounds, for example, 4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0Recommanded Product: 20485-41-0).

4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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: 20485-41-0

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

Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles was written by Xie, Zengyang;Chen, Ruijiao;Ma, Mingfang;Kong, Lingdong;Liu, Jun;Wang, Cunde. And the article was included in Applied Organometallic Chemistry in 2019.Application of 15864-32-1 This article mentions the following:

An efficient and practical C-N bond formation methodol. for the synthesis of N-(alkyl)benzothiazoles I [R = H, 4-Me, 6-Br, etc.; R¹ = n-Pr, Ph, 4-MeOC₆H₄, etc.] and N-(alkyl)thiazoles II [R² = H, Me; R³ = Ph, 2-MeC₆H₄, 2-naphthyl, etc.; R²R³ = (CH₂)₅; R⁴ = H, 4-Me, 5-Me] was developed via Cu-catalyzed one-pot two-step cross-coupling of 2-aminobenzothiazoles/2-aminothiazoles and aldehydes/ketones with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups. A variety of functionalized benzothiazoles/thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol. In the experiment, the researchers used many compounds, for example, 2-Amino-6-bromobenzothiazole (cas: 15864-32-1Application of 15864-32-1).

2-Amino-6-bromobenzothiazole (cas: 15864-32-1) 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. 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 of 15864-32-1

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

Design, synthesis and biological activity of tetrazole-bearing uric acid transporter 1 inhibitors was written by Cai, Wenqing;Liu, Wei;Xie, Yafei;Wu, Jingwei;Liu, Yuqiang;Liu, Changying;Xu, Weiren;Tang, Lida;Wang, Jianwu;Zhao, Guilong. And the article was included in Chemical Research in Chinese Universities in 2017.Category: thiazole This article mentions the following:

Systematic structure-activity relationship(SAR) exploration of a moderately active tetrazole-bearing lesinurad-based hit 1f led to the discovery of a potent uric acid transporter 1(URAT1) inhibitor 1i, which possessed a novel mol. skeleton and was 11-fold more potent than the parent lesinurad against human URAT1 in-vitro (IC₅₀=0.66 μmol/L for 1i vs. 7.18 μmol/L for lesinurad). In the experiment, the researchers used many compounds, for example, 5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (cas: 878671-96-6Category: thiazole).

5-Amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol (cas: 878671-96-6) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

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

Halides Held by Bifurcated Chalcogen-Hydrogen Bonds. Effect of μ_(S,N-H)Cl Contacts on Dimerization of Cl(carbene)Pd^II Species was written by Mikherdov, Alexander S.;Novikov, Alexander S.;Kinzhalov, Mikhail A.;Boyarskiy, Vadim P.;Starova, Galina L.;Ivanov, Alexander Yu.;Kukushkin, Vadim Yu.. And the article was included in Inorganic Chemistry in 2018.Synthetic Route of C9H7ClN2S This article mentions the following:

Addition of 2-thiazolamines with palladium bis-isonitrile complex cis-[PdCl₂(CNCy)₂] (1) produces acyclic diaminocarbene complexes I (R¹ = Ph, 4-MeC₆H₄, 4-FC₆H₄, 4-ClC₆H₄, 3,4-F₂C₆H₃; R² = H), dimerized by hydrogen bonds. The reaction of 1 with thiazol-2-amines leads to the C,N-chelated diaminocarbene-like complexes [PdCl{C(N(H)4,5-R₂-thiazol-2-yl)NHCy}(CNCy)] in the case of 4,5-R₂-thiazol-2-amines or gives the diaminocarbene species I for the reaction with 4-aryl-substituted thiazol-2-amines. Inspection of the single-crystal X-ray diffraction data for I suggests that the structures of all these species exhibit previously unrecognized bifurcated chalcogen-hydrogen bonding μ_(S,N-H)Cl and also Pd^II···Pd^II metallophilic interactions. These noncovalent interactions collectively connect two sym. located mols. resulting in their solid-state dimerization. The existence of the μ_(S,N-H)Cl system and its strength (6-9 kcal/mol) were addnl. verified/estimated by a Hirshfeld surface anal. and DFT calculations combined with a topol. anal. of the electron d. distribution within the formalism of Bader’s theory (AIM method) and NBO anal. The observed noncovalent interactions are jointly responsible for the dimerization of I not only in the solid phase but also in CHCl₃ solutions, as predicted theor. by DFT calculations and confirmed exptl. by FTIR, HRESI-MS, ¹H NMR, and diffusion coefficient NMR measurements. Available CCDC data were processed under the new moiety angle, and the observed μ_(S,E-H)Cl systems were classified accordingly to E (E = N, O, C) type atoms. In the experiment, the researchers used many compounds, for example, 4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3Synthetic Route of C9H7ClN2S).

4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3) 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. 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 C9H7ClN2S

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