Day: February 22, 2023

An overview of levamisole hydrochloride with immuno-stimulant activity was written by Biswajit, Das;Suvakanta, Dash;Chandra, Choudhury Ramesh;Jashabir, Chakraborty. And the article was included in American Journal of Pharmacy and Health Research in 2014.Reference of 16595-80-5 This article mentions the following:

Levamisole, marketed as the hydrochloride salt under the trade name Ergamisol (R12564), is an anti helminthic and immunomodulator belonging to a class of synthetic imidazo-thiazole derivatives It was discovered in 1966 at Belgium’s Janssen pharmaceutica, where it was prepared initially in the form of its racemate called tetramisole. The two stereoisomers of tetramisole were subsequently synthesized, and the levorotatory isomer was given the name levamisole. Levamisole has been used in humans to treat parasitic worm infections, and has been studied in combination with other forms of chemotherapy for colon cancer, melanoma, and head and neck cancer. In some of the leukemic cell line studies, both levamisole and tetramisole showed similar effect. Effective studies need to be undertaken to study the full potential of levamisole in Immunostimulation activities and immuno synergestic effect of Levamisole with combination to natural polysaccharides. In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride (cas: 16595-80-5Reference of 16595-80-5).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride (cas: 16595-80-5) 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. 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 16595-80-5

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

Lack of Detection of the Analgesic Properties of PF-05089771, a Selective Na_v1.7 Inhibitor, Using a Battery of Pain Models in Healthy Subjects was written by Siebenga, Pieter;van Amerongen, Guido;Hay, Justin L.;McDonnell, Aoibhinn;Gorman, Donal;Butt, Richard;Groeneveld, Geert Jan. And the article was included in Clinical and Translational Science in 2020.Computed Properties of C18H12Cl2FN5O3S2 This article mentions the following:

The aim was to demonstrate analgesic properties of a potent selective Na_v1.7 sodium channel blocker, PF-05089771, alone and concomitantly with pregabalin in healthy subjects using a battery of human evoked pain models. This was a double-blind, double-dummy, randomized, placebo-controlled, five-period cross-over study with PF-05089771 alone and PF-05089771 concomitantly with pregabalin as treatment arms with pregabalin, ibuprofen, and placebo as control arms (NCT02349607). A battery of human evoked pain models was used to investigate analgesic properties of PF-05089771. Twenty-five subjects were enrolled in the study of which 23 subjects completed all five periods. PF-05089771 alone did not differ from placebo on the primary pain end points. The same holds when comparing PF-05089771 concomitantly with pregabalin and pregabalin alone. Pregabalin showed significant effects relative to placebo on thermal pain on the normal skin and UVB skin (least squares means with 90% confidence interval: 0.63 (0.32-0.93) and 0.53 (0.11-0.96)), pressure stimulation (1.10 (1.04-1.18)), and cold pressor (1.22 (1.14-1.32)). Ibuprofen demonstrated significant effects on thermal pain UVB skin (1.26 (0.82-1.70)) and pressure stimulation assessment (1.08 (1.01-1.15)), consistent with historical results. This study did not demonstrate analgesic properties of PF-05089771 alone or concomitantly with pregabalin in a battery of pain models. In the experiment, the researchers used many compounds, for example, 4-(2-(3-Amino-1H-pyrazol-4-yl)-4-chlorophenoxy)-5-chloro-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide (cas: 1235403-62-9Computed Properties of C18H12Cl2FN5O3S2).

4-(2-(3-Amino-1H-pyrazol-4-yl)-4-chlorophenoxy)-5-chloro-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide (cas: 1235403-62-9) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Computed Properties of C18H12Cl2FN5O3S2

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

Genomic landscape of drug response reveals mediators of anthelmintic resistance was written by Doyle, Stephen R.;Laing, Roz;Bartley, David;Morrison, Alison;Holroyd, Nancy;Maitland, Kirsty;Antonopoulos, Alistair;Chaudhry, Umer;Flis, Ilona;Howell, Sue;McIntyre, Jennifer;Gilleard, John S.;Tait, Andy;Mable, Barbara;Kaplan, Ray;Sargison, Neil;Britton, Collette;Berriman, Matthew;Devaney, Eileen;Cotton, James A.. And the article was included in Cell Reports in 2022.Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole This article mentions the following:

Like other pathogens, parasitic helminths can rapidly evolve resistance to drug treatment. Understanding the genetic basis of anthelmintic drug resistance in parasitic nematodes is key to tracking its spread and improving the efficacy and sustainability of parasite control. Here, we use an in vivo genetic cross between drug-susceptible and multi-drug-resistant strains of Haemonchus contortus in a natural host-parasite system to simultaneously map resistance loci for the three major classes of anthelmintics. This approach identifies new alleles for resistance to benzimidazoles and levamisole and implicates the transcription factor cky-1 in ivermectin resistance. This gene is within a locus under selection in ivermectin-resistant populations worldwide; expression analyses and functional validation using knockdown experiments support that cky-1 is associated with ivermectin survival. Our work demonstrates the feasibility of high-resolution forward genetics in a parasitic nematode and identifies variants for the development of mol. diagnostics to combat drug resistance in the field. In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

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

Synthesis of N-Substituted Methyl 4H-Thieno[3,2-b]pyrrole-5-carboxylates was written by Torosyan, S. A.;Gimalova, F. A.;Zagitov, V. V.;Erastov, A. S.;Miftakhov, M. S.. And the article was included in Russian Journal of Organic Chemistry in 2018.Formula: C8H7NO2S This article mentions the following:

The alkylation of Me 4H-thieno[3,2-b]pyrrole-5-carboxylate with Me iodide and allyl, propargyl and benzyl bromides in the presence of sodium hydride in THF afforded the corresponding N-substituted derivatives I (R = Me, CH₂=CHCH₂, CH≡CCH₂, Bn). Some reactions of the alkylation products were studied. In the experiment, the researchers used many compounds, for example, Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (cas: 82782-85-2Formula: C8H7NO2S).

Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (cas: 82782-85-2) 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.Formula: C8H7NO2S

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

Direct C-H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)-N-heterocyclic Carbene Complexes was written by Kaloglu, Murat;Kaloglur, Nazan;Oezdemir, Ismail. And the article was included in Chinese Journal of Chemistry in 2018.Computed Properties of C14H11NS This article mentions the following:

Herein, a series of novel palladium(II)-NHC complexes (NHC=N-heterocyclic carbene) were synthesized. The structures of all novel complexes were characterized by ¹H NMR, ¹³C NMR, FT-IR spectroscopy and elemental anal. techniques. These palladium(II)-NHC complexes were tested as efficient catalysts in the direct C-H bond activation of benzoxazole and benzothiazole with aryl bromides in the presence of 1 mol% catalyst loading at 150 °C for 4 h. Under the given conditions, various aryl bromides were successfully applied as the arylating reagents to achieve the 2-arylbenzoxazoles and 2-arylbenzothiazoles in acceptable to high yields. In the experiment, the researchers used many compounds, for example, 2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3Computed Properties of C14H11NS).

2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3) 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.Computed Properties of C14H11NS

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

Identification and Categorization of Volatile Sulfur Flavor Compounds in Roasted Malts and Barley was written by Parr, Hebe;Bolat, Irina;Cook, David. And the article was included in Journal of the American Society of Brewing Chemists.Recommanded Product: 2-Ethoxythiazole This article mentions the following:

We report for the first time the application of HS-SPME-GC coupled with sulfur-specific pulsed flame photometric detection to sensitively analyze the volatile sulfur compounds (VSC′s) present in drum roasted malt and barley samples typically used in brewing. Twenty-five VSC′s were identified across a range of 9 roasted products produced from barley/malt. Thiophenes (n = 10) were a major class of heterocyclic sulfur compounds identified, along with thiazoles (n = 4), and thiofurans (n = 2). Quant. (n = 18) and semi-quant. (n = 6) data are reported for VSC′s across this product range. Principal Component Anal. (PCA) of data clearly identified (PC1) that heterocyclic sulfur compounds were formed in products processed at high temperatures (>170 °C) under dry conditions (roasted barley, chocolate and black malts). Whereas compounds such as Me dithiolane and Me Pr sulfide were associated primarily with lower temperature finished products (crystal, amber and cara malts). Pathways for the generation of observed VSC′s are considered alongside typical roasting conditions employed in the manufacture of these products. Concentrations of VSC′s identified will certainly contribute characteristic aromas to the roasted products themselves. The transfer of VSC′s from the grist into finished beer, and their sensory impact in a range of beer styles, remains to be determined In the experiment, the researchers used many compounds, for example, 2-Ethoxythiazole (cas: 15679-19-3Recommanded Product: 2-Ethoxythiazole).

2-Ethoxythiazole (cas: 15679-19-3) 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.Recommanded Product: 2-Ethoxythiazole

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

Modulation of ligand responses by coupling of α_2A-adrenoceptors to diverse G_α-proteins was written by Pauwels, P. J.;Tardif, S.;Colpaert, F. C.;Wurch, T.. And the article was included in Biochemical Pharmacology in 2001.Application In Synthesis of 6-Allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine dihydrochloride This article mentions the following:

The hypothesis that different signaling may be mediated via a single α_2A-adrenoceptor (α_2A AR) subtype was investigated by challenging α₂ AR ligands in combination with diverse recombinant weight, mutant, and chimeric G_α-proteins. Possible coupling of α_2A AR to endogenous G_αi/o-proteins in CHO-K1 cells was excluded by measuring pertussis toxin (PTX)-resistant [³⁵S]GTPγS-binding responses as a common functional response to α_2A AR activation. (-)-Adrenaline (10 μM) displayed the highest magnitude of [³⁵S]GTPγS-binding response in the co-presence of a PTX-resistant G_αoCys³⁵¹Ile protein, whereas a decreased response was obtained with the mutant G_αi1/2-proteins. Replacement of the last six amino acids at the C-terminal portion of the G_αo-protein by the corresponding amino acid region of either the G_αz-, G_αs-, G_αq-, or G_α15-protein and co-expression with the α_2A AR resulted in similar maximal (-)-adrenaline-mediated [³⁵S]GTPγS-binding responses with these chimeric G_αo-proteins. The ligands D-medetomidine, BHT 920 (6-allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-ylamine) and (+)-RX 811059 (2-(2-ethoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl)-4,5-dihydro-1H-imidazole) were weakly active or virtually inactive at the chimeric G_αo/s-, G_αo/q-, and G_αo/15-proteins in contrast to the G_αo/z-protein. Furthermore, combining the constitutively active mutant Thr³⁷³Lys α_2A AR with these chimeric G_αo-proteins enhanced the apparent intrinsic activity of D-medetomidine and BHT 920. A similar observation was made using the corresponding fusion proteins, where the stoichiometry of the mutant α_2A AR to the chimeric G_αo-protein was fixed at 1.0. These data indicate that a single ligand may display different magnitudes of activation at the α_2A AR subtype coupled to chimeric G_αo proteins under controlled conditions of α_2A AR: G_αo-protein expression. In the experiment, the researchers used many compounds, for example, 6-Allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine dihydrochloride (cas: 36085-73-1Application In Synthesis of 6-Allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine dihydrochloride).

6-Allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine dihydrochloride (cas: 36085-73-1) 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.Application In Synthesis of 6-Allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine dihydrochloride

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

MNPs@SiO₂-Pr-AP: A new catalyst for the synthesis of 2-amino-4-aryl thiazole derivatives was written by Ghorbani-Vaghei, Ramin;Alavinia, Sedigheh;Merati, Zohreh;Izadkhah, Vida. And the article was included in Applied Organometallic Chemistry in 2018.Formula: C9H8N2OS This article mentions the following:

Magnetically recoverable nano-magnetic catalyst supported with functionalized (n-propyl)-4-amino-pyridine silica (MNPs@SiO₂-Pr-AP) was synthesized and characterized using different techniques. A simple and efficient synthesis of 2-amino-4-aryl thiazoles I [R = H, 4-Cl, 3-NO₂, etc, X = CH, N] was described via condensation of acetophenones and thiourea using three different types of catalytic systems including N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N’-dibromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and a combination of TBBDA and MNPs@SiO₂-Pr-AP. The results showed that, the use of TBBDA along with the MNPs@SiO₂-Pr-AP gains the highest yields of the products in the shortest reaction time. In the experiment, the researchers used many compounds, for example, 4-(2-Amino-4-thiazolyl)phenol (cas: 57634-55-6Formula: C9H8N2OS).

4-(2-Amino-4-thiazolyl)phenol (cas: 57634-55-6) 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. 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.Formula: C9H8N2OS

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

Ring transformations of heterocyclic compounds. XVII. 2-(2,4,6-triarylphenyl) substituted dihydro-1H-imidazolium, dihydrothiazolium and thiazolium salts from 2-methyl derivatives by pyrylium and thiopyrylium ring transformations was written by Zimmermann, Thomas. And the article was included in Journal of Heterocyclic Chemistry in 1999.Category: thiazole This article mentions the following:

Some new 2-(2,4,6-triarylphenyl)-4,5-dihydro-1H-imidazolium perchlorates, -4,5-dihydrothiazolium perchlorates and -thiazolium perchlorates were obtained from their 2-Me analogs by a 2,6-[C₅+C] ring transformation of 2,4,6-triarylpyrylium and -thiopyrylium salts in ethanol in the presence of an appropriate base. Spectroscopic data of the transformation products and structural influences on their formation via anhydrobases of the triarylpyrylium and -thiopyrylium salts are discussed. In the experiment, the researchers used many compounds, for example, 2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1Category: thiazole).

2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1) 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 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.Category: thiazole

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

Halogen-substituted thiazole derivatives as corrosion inhibitors for mild steel in 0.5 M sulfuric acid at high temperature was written by Gong, Weinan;Xu, Bin;Yin, Xiaoshuang;Liu, Ying;Chen, Yun;Yang, Wenzhong. And the article was included in Journal of the Taiwan Institute of Chemical Engineers in 2019.Reference of 2103-99-3 This article mentions the following:

The inhibitory effects of three halogen-substituted thiazole derivatives named 2-amino-4-(4-fluorophenyl)-thiazole (FPT), 2-amino-4-(4-chlorophenyl)-thiazole (CPT) and 2-amino-(4-bromophenyl)-thiazole (BPT) on mild steel corrosion were investigated in 0.5 M H₂SO₄ from 30°C to 60°C. Electrochem. measurements demonstrated that these thiazoles can effectively inhibit the corrosion of mild steel in 0.5 M H₂SO₄ solution at 30°C. With the increase of temperature, the inhibition efficiency (η) of FPT at 60°C reduced to 22.62% while those of CPT and BPT under the same temperature were nearly unchanged, which were as high as 95.16% and 95.45%, resp. The adsorptions of three thiazoles on the surface of mild steel were all found to adhere to Langmuir adsorption isotherm at 30°C while only CPT and BPT obeyed at 60°C. Quantum calculations results indicated that CPT and BPT had the better adsorption ability on mild steel than FPT. Mol. dynamic stimulations were taken out to investigate the adsorption configurations of three thiazoles on the surface of Fe (0 0 1) at 30°C and 60°C, and the results implied that the binding energy of protonated BPT and CPT were nearly unchanged at studied temperatures while that of protonated FPT apparently became lower at 60°C. In the experiment, the researchers used many compounds, for example, 4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3Reference of 2103-99-3).

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

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