Tag: 100-200

Discovery of a New Class of Potent, Selective, and Orally Bioavailable CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases was written by Crosignani, Stefano;Page, Patrick;Missotten, Marc;Colovray, Veronique;Cleva, Christophe;Arrighi, Jean-Francois;Atherall, John;Macritchie, Jackie;Martin, Thierry;Humbert, Yves;Gaudet, Marilene;Pupowicz, Doris;Maio, Maurizio;Pittet, Pierre-Andre;Golzio, Lucia;Giachetti, Claudio;Rocha, Cynthia;Bernardinelli, Gerald;Filinchuk, Yaroslav;Scheer, Alexander;Schwarz, Matthias K.;Chollet, Andre. And the article was included in Journal of Medicinal Chemistry in 2008.Computed Properties of C5H6BrNS The following contents are mentioned in the article:

A novel chem. class of potent chemoattractant receptor-homologous expressed on Th2 lymphocytes (CRTH2 or DP2) antagonists is reported. An initial and moderately potent spiro-indolinone compound (I) was found during a high-throughput screening campaign. Structure-activity relationship (SAR) investigation around the carboxylic acid group revealed that changes in this part of the mol. could lead to a reversal of functional activity, yielding weakly potent agonists. SAR investigation of the succinimide functional group led to the discovery of several single-digit nanomolar antagonists. The potency of these compounds was confirmed in a human eosinophil chemotaxis assay. Moreover, compounds II and III were shown to possess pharmacokinetic properties suitable for development as an orally bioavailable drug. This study involved multiple reactions and reactants, such as 4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5Computed Properties of C5H6BrNS).

4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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 C5H6BrNS

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

Cyclopropanation of 3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-diones was written by Lack, Oliver;Martin, Rainer E.. And the article was included in Tetrahedron Letters in 2005.Related Products of 74704-39-5 The following contents are mentioned in the article:

A two step parallel synthesis protocol for the preparation of 1N-substituted spirobenzodiazepineones is described. Treatment of 4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione with a series of alkyl halides using a microwave-assisted heating protocol provided N-derivatized compounds, which were transformed to the corresponding cyclopropylamines employing modified Kulinkovich-type reaction conditions. X-ray structural anal. gave conclusive evidence of the newly created spiro center and revealed a significant flattening of the seven-membered ring system compared with the benzodiazepinedione system providing a characteristically different pattern of bond exit vectors. The physicochem. parameters log D, pK_a, solubility, and membrane permeability of both cyclopropanated and precursor compounds were assessed. This study involved multiple reactions and reactants, such as 4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5Related Products of 74704-39-5).

4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5) 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.Related Products of 74704-39-5

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

Phenyl thiazolyl urea and carbamate derivatives as new inhibitors of bacterial cell-wall biosynthesis was written by Francisco, Gerardo D.;Li, Zhong;Albright, J. Donald;Eudy, Nancy H.;Katz, Alan H.;Petersen, Peter J.;Labthavikul, Pornpen;Singh, Guy;Yang, Youjun;Rasmussen, Beth A.;Lin, Yang-I.;Mansour, Tarek S.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.Product Details of 303994-99-2 The following contents are mentioned in the article:

Over 50 Ph thiazolyl urea and carbamate derivatives were synthesized for evaluation as new inhibitors of bacterial cell-wall biosynthesis. Many of them demonstrated good activity against MurA and MurB and gram-pos. bacteria including MRSA, VRE and PRSP. (3,4-Difluorophenyl)(5-cyanothiazolyl)urea with clog P of 2.64 demonstrated antibacterial activity against both gram-pos. and gram-neg. bacteria. The activity of these (phenyl)(thiazolyl)urea and (thiazolyl)carbamate derivatives was also compared to 3-[[[(3,4-dichlorophenyl)amino]carbonyl]amino]-2-thiophenecarboxylic acid Me ester, 5-[[[(3,4-dichlorophenyl)amino]carbonyl]amino]-1-methyl-1H-pyrazole-4-carboxylic acid Me ester, N-(3,4-dichlorophenyl)-N‘-(2-pyridinyl)urea, and some other compounds Antibacterial activity was screened against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococus (VRE), penicillin-resistant Streptococcus pneumoniae (PRSP). Mol. modeling studies were carried out to explore binding preferences within this compound series in the MurB structure. This study involved multiple reactions and reactants, such as 2-Amino-4-(tert-butyl)thiazole-5-carbonitrile (cas: 303994-99-2Product Details of 303994-99-2).

2-Amino-4-(tert-butyl)thiazole-5-carbonitrile (cas: 303994-99-2) 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.Product Details of 303994-99-2

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

Identification of N, C-capped di- and tripeptides as selective immunoproteasome inhibitors was written by Nan, Guanglei;Huang, Lei;Li, Yunxuan;Yang, Yajun;Yang, Ying;Li, Ke;Lai, Fangfang;Chen, Xiaoguang;Xiao, Zhiyan. And the article was included in European Journal of Medicinal Chemistry in 2022.Synthetic Route of C7H4N2O2S The following contents are mentioned in the article:

A series of N, C-capped di- and tripeptides were designed as selective immunoproteasome inhibitors based on the known inhibitor 4-CA. Forty-eight new compounds were synthesized and evaluated, and the structure-activity relationship (SAR) of this compound class as β5i selective inhibitors were explored. Most of these compounds showed significant inhibition against the β5i subunit of the immunoproteasome and the most potent β5i inhibitor (15) showed an IC₅₀ of 0.94 nM. A selective β5i inhibitor (54) with over 500-fold β5i/β5c selectivity was identified. Three of the inhibitors were found to selectively inhibit β5i and β5c, and showed no noticeable inhibition against the other four subunits. Six inhibitors with significant inhibitory activity against the HCT-116 cells were recognized, and the most active inhibitors, 14 and 50, showed IC₅₀ values of 0.46 μM and 0.16 μM, resp. Some selective β5i inhibitors exhibited significant inhibitory effects on the release of the cytokines TNF-α and IL-6. The results not only afford effective chem. tools to elucidate the relationships between subunit selectivity and pharmacol. profiles, but also offer useful clues for further optimization and development of selective immunoproteasome inhibitors. This study involved multiple reactions and reactants, such as 2-Cyano-3-(thiazol-2-yl)acrylic acid (cas: 1567534-28-4Synthetic Route of C7H4N2O2S).

2-Cyano-3-(thiazol-2-yl)acrylic acid (cas: 1567534-28-4) 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.Synthetic Route of C7H4N2O2S

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

12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents was written by Nicolaou, K. C.;Rhoades, Derek;Wang, Yanping;Bai, Ruoli;Hamel, Ernest;Aujay, Monette;Sandoval, Joseph;Gavrilyuk, Julia. And the article was included in Journal of the American Chemical Society in 2017.Name: 4-(Bromomethyl)-2-methylthiazole The following contents are mentioned in the article:

The synthesis and biol. evaluation of a series of 12,13-aziridinyl epothilone B analogs is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic Me ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kurti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications. This study involved multiple reactions and reactants, such as 4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5Name: 4-(Bromomethyl)-2-methylthiazole).

4-(Bromomethyl)-2-methylthiazole (cas: 74704-39-5) 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: 4-(Bromomethyl)-2-methylthiazole

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

On September 1, 2019, Sami, Yuichi; Morita, Masataka; Kubota, Hirokazu; Hirabayashi, Ryoji; Seo, Ryushi; Nakagawa, Nobuaki published an article.Synthetic Route of 2010-06-2 The title of the article was Discovery of a novel orally active TRPV4 inhibitor: Part 1. Optimization from an HTS hit. And the article contained the following:

Novel oral TRPV4 inhibitors were prepared and their potential for pain management in osteoarthritis discussed. The experimental process involved the reaction of 4-Phenylthiazol-2-amine(cas: 2010-06-2).Synthetic Route of 2010-06-2

The Article related to oral trpv4 inhibitor preparation analgesic osteoarthritis, Pharmacology: Structure-Activity and other aspects.Synthetic Route of 2010-06-2

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

On May 21, 2008, Brak, Katrien; Doyle, Patricia S.; McKerrow, James H.; Ellman, Jonathan A. published an article.COA of Formula: C8H7NOS The title of the article was Identification of a New Class of Nonpeptidic Inhibitors of Cruzain. And the article contained the following:

Cruzain is the major cysteine protease of Trypanosoma cruzi, which is the causative agent of Chagas disease and is a promising target for the development of new chemotherapy. With the goal of developing potent nonpeptidic inhibitors of cruzain, the substrate activity screening (SAS) method was used to screen a library of protease substrates initially designed to target the homologous human protease cathepsin S. Structure-based design was next used to further improve substrate cleavage efficiency by introducing addnl. binding interactions in the S3 pocket of cruzain. The optimized substrates were then converted to inhibitors by the introduction of cysteine protease mechanism-based pharmacophores. Inhibitor 38 was determined to be reversible even though it incorporated the vinyl sulfone pharmacophore that is well documented to give irreversible cruzain inhibition for peptidic inhibitors. The previously unexplored β-chloro vinyl sulfone pharmacophore provided mechanistic insight that led to the development of potent irreversible acyl- and aryl-oxymethyl ketone cruzain inhibitors. For these inhibitors, potency did not solely depend on leaving group pKa, with 2,3,5,6-tetrafluorophenoxymethyl ketone 54 identified as one of the most potent inhibitors with a second-order inactivation constant of 147,000 s-1 M-1. This inhibitor completely eradicated the T. cruzi parasite from mammalian cell cultures and consequently has the potential to lead to new chemotherapeutics for Chagas disease. The experimental process involved the reaction of Benzo[d]thiazol-6-ylmethanol(cas: 19989-66-3).COA of Formula: C8H7NOS

The Article related to nonpeptidic inhibitor cruzain structure chagas disease, Pharmacology: Structure-Activity and other aspects.COA of Formula: C8H7NOS

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

On March 31, 2022, Li, Xinzhi; Liu, Shao-Quan published an article.SDS of cas: 24295-03-2 The title of the article was Modulation of aroma compounds in yeast and lactic acid bacterium co-fermented pork hydrolysates by thermal treatment and addition of aroma precursors (cysteine and xylose). And the article contained the following:

The objective of this study was to evaluate the effectiveness of using enzymic hydrolysis and microbial fermentation coupled with thermal treatment methods in valorising a type of industrially generated meat byproduct: pork trimmings, so as to produce a value-added meat-based flavouring. The pork trimmings were first hydrolyzed using a protease (Flavourzyme) under optimized conditions and then fermented into liquid hydrolyzates with mixed Lactobacillus fermentum and Pichia kluyveri; afterwards, xylose and cysteine were added to the fermented hydrolyzates for heat treatment. A characteristic “savoury and roasted-meat” aroma was produced due to the formation of potent sulfur-containing volatile compounds such as 2-furfurylthiol and methionol, though the browning intensity was inhibited due to the presence of cysteine. The thermal treatment did not significantly affect the fruity and sweet-smelling ester volatiles such as isoamyl acetate and hexyl acetate that resulted from microbial fermentation The decreases of amino acids and xylose might be due to their active participation in the Maillard reaction. The produced pork hydrolyzates that imparted a unique aroma could be applied as a flavor enhancer or seasoning in the food industry. The experimental process involved the reaction of 2-Acetylthiazole(cas: 24295-03-2).SDS of cas: 24295-03-2

The Article related to cysteine xylose aroma compound yeast lactic acid pork, Food and Feed Chemistry: Other and other aspects.SDS of cas: 24295-03-2

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

On December 31, 2022, Wang, Lin; Li, Cong; Al-Dalali, Sam; Liu, Yiyang; Zhou, Hui; Chen, Conggui; Xu, Baocai; Wang, Ying published an article.Product Details of 24295-03-2 The title of the article was Characterization of key aroma compounds in traditional beef soup. And the article contained the following:

This study aimed to identify the characteristic aroma compounds of beef soup and analyze the differences between their aroma. Seven beef soup samples were analyzed by sensory evaluation combined with gas chromatog.-mass spectrometry (GC-MS) and electronic nose (E-nose). A total of 80 volatile compounds were identified, and seven key aroma compounds in beef soup samples were determined by odor activity value, sensory evaluation, aroma recombination and omission experiments They were linalool, (E)-3,7-dimethyl-2,6-octadien-1-ol, nonanal, (E)-2-octenal, 3,7-dimethyl-2,6-octadienal, 2-acetylthiazole and estragole. The panelists described the organoleptic characteristics of beef soup as beef meaty, spice, fatty, caramel, and roasted. GC-MS and E-nose combined with principal component anal. showed different aroma profiles among beef soup samples. A total of 30 potential differential markers were screened by partial least squares discriminant anal. The difference between samples was mainly caused by the type and content of compounds The experimental process involved the reaction of 2-Acetylthiazole(cas: 24295-03-2).Product Details of 24295-03-2

The Article related to beef soup aroma compound, Food and Feed Chemistry: Other and other aspects.Product Details of 24295-03-2

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

Mugherli, Laurent; Burchak, Olga N.; Balakireva, Larissa A.; Thomas, Aline; Chatelain, Francois; Balakirev, Maxim Y. published an article in 2009, the title of the article was In Situ Assembly and Screening of Enzyme Inhibitors with Surface-Tension Microarrays.Synthetic Route of 64987-16-2 And the article contains the following content:

Hundreds of reactions were conducted in parallel in droplets maintained on a glass slide through differential surface tension in a new approach to submicroliter-scale synthesis. This surface-tension microarray was applied to the in situ assembly of thousands of derivatives of phenylboronic acid and their profiling against the NS3/4A protease of the hepatitis C virus. Several potent inhibitors of the enzyme were identified. The experimental process involved the reaction of Methyl 2-(2-aminothiazol-4-yl)acetate(cas: 64987-16-2).Synthetic Route of 64987-16-2

The Article related to drug screening ns3 4a protease inhibitor preparation microarray, Pharmacology: Methods and other aspects.Synthetic Route of 64987-16-2

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