Month: February 2023

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

Effect of primary amines of binuclear, noncondensed ring compounds on the growth of tubercle bacilli was written by Erlenmeyer, H.;Becker, C.;Sorkin, E.;Bloch, H.;Suter, E.. And the article was included in Helvetica Chimica Acta in 1947.Formula: C9H7NS This article mentions the following:

C.A. 41, 6925h. A systematic series of compounds similar in structure to p-H₂NC₆H₄Ph (I), with a tertiary C atom para to the NH₂ group, was prepared to test the influence of the tertiary linkage on tuberculostatic activity. The growth of tubercle bacillus in surface cultures on Lockemann medium is totally inhibited by 1-25 × 10^-7 M I. In comparison with 2 × 10^-4 M Na salicylate, I is 1600 times as effective in restricting the growth of tubercle bacillus in vitro, i.e., I has a salicylate number (SN) 1600. The selected compounds, 2-(p-aminophenyl)thiazole (II), 4-(p-aminophenyl)thiazole (III), 5-(p-aminophenyl)thiazole (IV), and the isoteric 3-(p-aminophenyl)pyridine (V), show total inhibition of Lockemann surface cultures at 2.5 × 10^-7, 5 × 10^-7, 1 × 10^-7, and 3.3 × 10^-7 M, resp., and have 800, 400, 2000, and 600 SN. The linkage relationship existing in I and the 3 thiazoles was demonstrated in the syntheses. The nitration of the corresponding phenylthiazoles with HNO₃ and H₂SO₄ at 0° gave the p-NO₂ derivative exclusively whereas nitration of BzOH yields only the m-NO₂ compound PhCSNH₂ (60 g.) and 50 g. dipolymerized BrCH₂CHO in 180 cc. absolute alc. containing 3 drops of piperidine were refluxed 10 hrs. The alc.-free reaction mixture was steam-distilled in the presence of 2 N Na₂CO₃ and the distillate was extracted with ether. Distillation of the oil from the evaporated dried extract yielded 47 g. (72%) 2-phenylthiazole, b₁₈ 125-8°, nitrated to give 80% of the corresponding 2-(p-nitrophenyl)thiazole, m. 147-8°. Reduction with Raney Ni in absolute alc. produced 2.75 g. (75%) II, m. 123-4°; Ac derivative, C₁₁H₁₀N₂OS, m. 140-1°; Bz derivative, C₁₆H₁₂N₂OS, m. 164-6°. The reduction of II gave orange crystals of 4,4′-di-2-thiazolylazoxybenzene, C₁₈H₁₂N₄OS₂, m. 234-5°. Nitration of 4-phenylthiazole produced 90% of needles of 4-(p-nitrophenyl)thiazole (VI), m. 177-8°, reduced to 83% III, m. 99-100°. As proof of structure, VI was degraded by oxidation with K₂Cr₂O₇ in H₂SO₄ to p-NO₂C₆H₄CO₂H in 62% yields. Bromination of 20 g. PhCH₂CHO in 100 cc. absolute CHCl₃ under CO₂ with 10 cc. Br 6 hrs. gave 32 g. of light-green oily PhCHBrCHO, converted according to Ger. pat. 670,131 (C.A. 33, 2909.5) with HCONH₂ and PS₅ in toluene to 14.5% 5-phenylthiazole (VII), m. 40-1°. Nitration of 2.5 g. VII gave 2.95 g. (92%) of crude nitration product, recrystallized from alc. to yellow needles of 5-(p-nitrophenyl)thiazole (VIII), C₉H₆N₂O₂S, m. 145-6°, oxidatively degraded to p-NO₂C₆H₄CO₂H. Catalytic reduction of 3.2 g. VIII with Raney Ni and recrystallization from H₂O produced 2.2 g. (80%) of colorless needles of IV, C₉H₈N₂S, m. 149.5-50.0°; BzO derivative m. 206°. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Formula: C9H7NS).

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. 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.Formula: C9H7NS

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

Radical reactivity in thiazoles. III. Synthesis of aryl thiazoles and their derivatives. An analytical study was written by Varnin, G.;Aune, J. P.;Dou, H. J. M.;Metzger, J.. And the article was included in Bulletin de la Societe Chimique de France in 1967.Name: 5-Phenylthiazole This article mentions the following:

Aryl- and arylalkylthiazoles were prepared and their uv, ir, and N.M.R. spectra determined Thus, according to the method of Gabriel, thioamides were prepared by treating 0.1 mole of an amide in dioxane with 1.5/5 mole P2S5 45 min. at 40°. Formation of the resultant thioamides was followed by thin layer chromatog. using silica GF-254 and C6H6 containing 5% EtOH. The obtained thioamide was treated with 0.1 mole of the carbonyl derivative at 60°, and the reaction mixture kept 2 hrs. at 100° and acidified, and dioxane was steam distilled The resulting reaction product was neutralized and steam distilled to give the corresponding thiazole. Higher yields of thiazoles were obtained by using absolute EtOH in the presence of fused NaOAc and drops of piperidine. The α-bromoketones were prepared by treating the corresponding ketones with Br2 at 50-5° in aqueous solution in the presence of KClO4 as described by Catch and D. F. Elliot. Bromination may be also carried by the use of NaOBr, or N-bromosuccinimide. The thiazoles (I) prepared are listed in the table. The prepared thiazoles were analyzed by gas chromatog. using 10% silicone SE 30 on 60/80 mesh fire brick. The retention volume for I were given at 200° and were compared with those obtained on 5% carbowax 20 M on chromosorb P 60/80 mesh. [TABLE OMITTED] The Rf and Rm values for I were given using silica DF-5 and (1:1) C6H6-CH2Cl2 eluant mixture or Al2O3 DF-5 and 55:15 heptane-CH2Cl2 eluant mixture thin layer chromatog. The conditions were given. The uv, ir, and N.M.R. spectra were discussed. 65 references. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Name: 5-Phenylthiazole).

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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Name: 5-Phenylthiazole

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

Absorption spectra of isomeric methyl- and phenylthiazoles and their simple and quaternary salts was written by Kornilov, M. Yu.;Aych, E. D.;Smeshko, L. I.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1973.Recommanded Product: 5-Phenylthiazole This article mentions the following:

The π-π* absorption maximum for the 2-, 4-, and 5-Me and the 2-, 4-, and 5-phenylthiazoles, their HCl salts, and the N-Me quaternary salts was determined Formation of the salt resulted in a 6-7 nm bathochromic shift for each of the methylthiazoles. The bathochromic shift was larger for 5-phenylthiazole and the quaternary salt of 4-phenylthiazole. The shifts were hypsochromic with 2-phenylthiazole. These changes are discussed in terms of steric hindrance and resonance. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 5-Phenylthiazole).

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

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

Transition-Metal-Free ipso-Arylative Condensation was written by Sinclair, Geoffrey S.;Kukor, Andrew J.;Imperial, Kevin Karl G.;Schipper, Derek J.. And the article was included in Macromolecules (Washington, DC, United States) in 2020.Category: thiazole This article mentions the following:

The development of economical synthetic methods remains an important step toward the widespread use of conjugated polymers. Most well-established methods require either prefunctionalization with organometallic reagents or the use of expensive transition-metal catalysts. We have shown that 2-hydroxyalkyl- and 2-hydroxyaryl-substituted thiazole N-oxides can proceed through an ipso-arylative condensation that yields bithiazole-containing conjugated small mols. and polymers. The use of 2-hydroxyaryl substituents enables access to a wide scope of thiazole N-oxide substrates and presents an economical route to the synthesis of bithiazole-based conjugated polymers with varying phys. and electronic properties. 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. 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

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

Exploration of novel piperazine or piperidine constructed non-covalent peptidyl derivatives as proteasome inhibitors was written by Zhuang, Rangxiao;Gao, Lixin;Lv, Xiaoqing;Xi, Jianjun;Sheng, Li;Zhao, Yanmei;He, Ruoyu;Hu, Xiaobei;Shao, Yidan;Pan, Xuwang;Liu, Shourong;Huang, Weiwei;Zhou, Yubo;Li, Jia;Zhang, Jiankang. And the article was included in European Journal of Medicinal Chemistry in 2017.SDS of cas: 55661-33-1 This article mentions the following:

A series of novel piperazine or piperidine-containing non-covalent peptidyl derivatives possessing a neopentyl-asparagine residue were designed, synthesized and evaluated as proteasome inhibitors. All target compounds were screened for their 20S proteasome chymotrypsin-like inhibitory activities, and 15 ones displayed more potent activities than carfilzomib with IC₅₀ values lower than 10 nM. Subsequently, the most potent 10 analogs were tested for their cytotoxic activities against two multiple myeloma (MM) cell lines RPMI-8226 and MM-1S. Based on these experiments, selected derivatives were further evaluated for their ex vivo and in vivo blood cell proteasome inhibitory activities. The most potential compound (I) (proteasome inhibition IC₅₀: 1.2 ± 0.1 nM) with potent anti-proliferation (IC₅₀: RPMI-8226 8.4 ± 0.8 nM; MM-1S: 6.3 ± 0.8 nM), ex vivo and in vivo activities also had a prolonged half life in plasma, which demonstrated that the enzymic stabilities of this series of compounds have been improved by constructing a six-membered ring into the peptide skeleton. All the experiments confirmed the correctness of design concept, which made this series of compounds potential leads for exploring new anti-MM drugs. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1SDS of cas: 55661-33-1).

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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.SDS of cas: 55661-33-1

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

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products was written by Xu, Hui;Ma, Biao;Fu, Zunyun;Li, Han-Yuan;Wang, Xing;Wang, Zhen-Yu;Li, Ling-Jun;Cheng, Tai-Jin;Zheng, Mingyue;Dai, Hui-Xiong. And the article was included in ACS Catalysis in 2021.Name: Benzothiazole-5-carboxylic acid This article mentions the following:

A palladium-catalyzed ligand-promoted alkynation of unstrained aryl ketones RC(O)R¹ (R = naphthalen-2-yl, 1-benzothiophen-5-yl, 4-(2H-1,2,3-triazol-2-yl)benzen-1-yl, etc.; R¹ = Me, n-Pr, Ph, etc.) have been reported. The protocol allows the alkynation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope for the synthesis of aryl-/terminal alkynes RCCR² (R² = 2-fluorophenyl, naphthalen-2-yl, thiophen-2-yl, etc.) and RCCH. The potential applications of this protocol in drug discovery and chem. biol. are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products e.g., I. More importantly, two different biol. important fragments R³CCR⁴ (R = 3-methoxy-4-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy)benzen-1-yl, 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalen-2-yl; R⁴ = 4-(dipropylsulfamoyl)phenyl) derived from a pharmaceutical and natural product could be connected by the consecutive alkynation of ketones CH₃(CH₂)₂C(O)R⁴. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone (1-[(17β)-17-(acetyloxy)estra-1,3,5(10)-trien-2-yl]ethanone) by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynation. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Name: Benzothiazole-5-carboxylic acid).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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. 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.Name: Benzothiazole-5-carboxylic acid

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

Second Generation Tetrahydroquinoline-Based Protein Farnesyltransferase Inhibitors as Antimalarials was written by Bendale, Pravin;Olepu, Srinivas;Suryadevara, Praveen Kumar;Bulbule, Vivek;Rivas, Kasey;Nallan, Laxman;Smart, Brian;Yokoyama, Kohei;Ankala, Sudha;Pendyala, Prakash Rao;Floyd, David;Lombardo, Louis J.;Williams, David K.;Buckner, Frederick S.;Chakrabarti, Debopam;Verlinde, Christophe L. M. J.;Van Voorhis, Wesley C.;Gelb, Michael H.. And the article was included in Journal of Medicinal Chemistry in 2007.Safety of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Substituted tetrahydroquinolines (THQs) have been previously identified as inhibitors of mammalian protein farnesyltransferase (PFT). Previously it was shown that blocking PFT in the malaria parasite led to cell death and that THQ-based inhibitors are the most potent among several structural classes of PFT inhibitors (PFTIs). THQ-based PFTIs, e.g., I, were synthesized and several compounds were discovered that inhibit the malarial enzyme in the sub- to low-nanomolar range and that block the growth of the parasite (P. falciparum) in the low-nanomolar range. This body of structure-activity data can be rationalized in most cases by consideration of the X-ray structure of one of the THQs bound to mammalian PFT together with a homol. structural model of the malarial enzyme. The results of this study provide the basis for selection of antimalarial PFTIs for further evaluation in preclin. drug discovery assays. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Safety of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

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

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