Day: October 14, 2022

Mayer, Ursula published the artcile< Catalase activity and resistance of Salmonella typhimurium against spiramycin>, Reference of 92276-38-5, the main research area is .

Of 11 strains of S. typhimurium, of known catalase activity and virulence, those rich in catalase were resistant or only moderately sensitive to spiramycin while those with low catalase content were all sensitive.

Zeitschrift fuer Hygiene und Infektionskrankheiten published new progress about Salmonella typhimurium. 92276-38-5 belongs to class triazoles, and the molecular formula is C5H3BrN4, Reference of 92276-38-5.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Mao, Yujian; Jiang, Jing; Yuan, Dandan; Chen, Xiuzhen; Wang, Yanan; Hu, Lihong; Zhang, Yinan published the artcile< Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy>, Computed Properties of 88088-95-3, the main research area is methyl naphthalene preparation regioselective DFT; naphthaldehyde potassium methyl trifluoroborate methylation palladium transient ligand catalyst.

Me groups widely exist in bioactive mols., and site-specific methylation has become a valuable strategy for their structural functionalization. Aiming to introduce this smallest alkyl handle, a highly regioselective peri- and ortho-C-H methylation of 1-naphthaldehyde by using a transient ligand strategy has been developed. A series of methyl-substituted naphthalene frameworks, e.g., 8-methyl-1-naphthaldehyde have been prepared in moderate to excellent yields. Mechanistic studies demonstrate that peri-methylation is controlled by the higher electronic d. of the peri-position of 1-naphthaldehyde as well as the formation of intermediary 5,6-fused bicyclic palladacycles, whereas exptl. studies and theor. calculations inferred that a 5-membered iridacycle at the ortho-position of 1-naphthaldehyde leads to energetically favorable ortho-methylation via an interconversion between the peri-iridacycle and ortho-iridacycle. Importantly, to demonstrate the synthetic utility of this method, was shown that this strategy can serve as a platform for the synthesis of multi-substituted naphthalene-based bioactive mols. and natural products.

Chemical Science published new progress about C-H bond activation. 88088-95-3 belongs to class triazoles, and the molecular formula is C19H13N9, Computed Properties of 88088-95-3.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Androsov, Dmitry A.; Neckers, Douglas C. published the artcile< Photochemical Study of Tris(benzotriazol-1-yl)methane>, Application of C19H13N9, the main research area is photochem trisbenzotriazolmethane.

Photodecomposition of tris(benzotrizol-1-yl)methane (1) in benzene gives [1-benzotryazol-1-yl-methylidene]biphenyl-2-ylamine (2) resulting from the loss of the benzotriazolyl radical and nitrogen followed by addition of benzene. Elimination of the second benzotriazolyl radical from 2 provides the biphenyl-2-ylmethyleneamine radical, which affords phenantridine (3) after ring closure. In contrast, the photolysis of 1 in methanol gives a high yield of benzotriazole (4).

Journal of Organic Chemistry published new progress about Azoles Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent). 88088-95-3 belongs to class triazoles, and the molecular formula is C19H13N9, Application of C19H13N9.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Graboyes, Harold; Day, Allan R. published the artcile< Metabolite analogs. VIII. Syntheses of some imidazopyridines and pyridotriazoles>, Application of C5H3BrN4, the main research area is .

2-Amino-5-bromopyridine (I), m. 136-7° (H2O or C6H6), was prepared by the method of Case (C.A. 41, 1672b). The 3-NO2 derivative (22.8 g.) of I added in portions to 76 g. SnCl2 in 200 cc. concentrated HCl with cooling, and the mixture heated 0.5 hr. on the steam bath, cooled, basified strongly with 40% aqueous NaOH, and filtered yielded 68% 3-NH2 derivative (II) of I, m. 163-4° (H2O), also obtained in 34% yield by reduction with Na2S2O4. II (5 g.) in 25 cc. 98-100% HCO2H refluxed 1 hr. and evaporated to dryness on the steam bath gave 57% 6-bromoimidazo[b]pyridine (III), m. 227-8° (H2O). Similarly were prepared: the 5-Me derivative (IV) of III, m. 204-5°; 7-Me derivative (V) of III, 262-3°; 5,7-di-Me derivative (VI) of III, 279-80° (decomposition); all in 100% yield. VI gave 75% VI.HCl, m. 308-9° (decomposition). II (5.64 g.) in 150 cc. warm H2O containing 5 cc. concentrated H2SO4 cooled below 10°, treated dropwise with stirring with 2.3 g. NaNO2 in 25 cc. H2O, stirred 1 hr., filtered, and the solid recrystallized from a large excess of 2N HCl yielded 83% 6-bromopyrido[2,3-d]-v-triazole (VI), m. 208-9°. The 6-Me derivative (VII) (93.5 g.) of I added with stirring to 400 cc. cold concentrated H2SO4, and the mixture warmed to 55°, treated dropwise at 55-60°, with 32 cc. concentrated HNO3 during 3 hrs., stirred 1 hr., poured into 1 kg. crushed ice, treated with 40% aqueous NaOH, and filtered gave 82% 3-NO2 derivative (VIII) of VII, yellow needles, m. 210-11° (BuOH), converted by the method described for II to 88% 6-Me derivative (IX) of II, m. 136-7° (H2O). IV (3.8 g.) in 150 cc. 1% aqueous NaOH hydrogenated 0.5 hr. at 50 lb. over 2 g. 5% Pd-C and 0.2 g. PtO2, filtered, neutralized with HCl, evaporated, the residue extracted with boiling PhMe, and the extract cooled yielded 36% 5-methylimidazo[b]pyridine (X), m. 218-19°. VI yielded similarly 43% 7-Me derivative of X, m. 217-18°. IX (4.04 g.) in 100 cc. 5% HCl treated dropwise with stirring at 5-10° with 1.73 g. NaNO2 in 25 cc. H2O, stirred 1 hr., and filtered gave 71% 5-Me derivative (XI) of VI, m. 201.5-202° (decomposition). Similarly were prepared from the corresponding diamines the following substituted pyrido[2,3-d]-v-triazoles (substituents, % yield, and m.p. given): 5,6-MeBr (XII), 74, 229-30° (decomposition); 5,7,6-Me2Br (XIII), 71, 190-1°; 5-SO2NH2, 85, 249° (decomposition). 2-Amino-4-methylpyridine (XIV) brominated by the method of Case (loc. cit.) yielded 69% 5-Br derivative (XV), m. 147-7.5° (cyclohexane). XV nitrated in the usual manner, poured onto crushed ice, adjusted with NH4OH to pH 5, and filtered yielded 75% 3-NO2 derivative (XVI) of XV, m. 168-9° (aqueous EtOH). XVI (23.2 g.) added gradually to 76 g. SnCl2 in 200 cc. concentrated HCl and worked up in the usual manner gave 73% 3-N2 analog of XVI, m. 161-2°, also obtained in 42% yield by reduction with Na2S2O4. V debrominated by hydrogenation during 7 hrs. yielded 100% 7-isomer of X, m. 146-7° (H2O or PhMe). 2-Acetamido-4,6-dimethyl-5-bromopyridine prepared by the method of Mariella and Belcher (C.A. 48, 2063a), hydrolyzed, and the resulting 2-amino-4,6-dimethyl-5-bromopyridine (XVII) nitrated, poured onto 1 kg. crushed ice, diluted with 1 l. H2O, and filtered 72% 3-NO2 derivative (XVIII) of XVII, m. 169-70°. XVIII reduced with SnCl2 and HCl 92% 3-H2 analog of XVIII, m. 183-4°. The 5,7-di-Me derivative of VI debrominated in the usual manner by hydrogenation yeilded 33% 5,7-dimethylpyrido[2,3-d]-v-triazole, m. 213-14°. 2-Amino-5-pyridinesulfonic acid (XIX) (54.2 g.) in 200 cc. concentrated H2SO4 treated dropwise at 50-5° with 16.4 cc. fuming HNO3, stirred 1 hr. at 50°, then until cooled to room temperature, poured onto 600 g. crushed ice, and filtered yielded 27-32% 3-;N2 derivative (XX) of XIX, decompose above 300°. XX (21.9 g.) added in small portions to 76 g. SnCl2 in 200 cc. concentrated HCl, heated 0.5 hr. on the steam bath, cooled, filtered, the residue suspended in 150 cc. 0.3N HCl, treated with H2S, filtered, and the hot filtrate cooled yielded 70% 3-NH2 analog (XXI) of XX, m. 308-9° (decomposition) (H2O). XXI (3.78 g.) in 25 cc. HCONH2 heated 2 hrs. with stirring, cooled, diluted with 50 cc. absolute EtOH and excess dry Et2O, filtered, and the residue refluxed 0.5 hr. with 50 cc. 2N HCl and cooled gave 62% imidazo[b]pyridine-6-sulfonic acid; m. above 360° (H2O). XXI (4.04 g.) in 100 cc. 5% HCl treated at 5-10° with 1.73 g. NaNO2 in 25 cc. H2O, stirred 2 hrs., evaporated in vacuo, the residue extracted with EtOH, and the extract diluted with dry Et2O yielded 67% pyrido[2,3-d]-v-triazole-6-sulfonic acid, decompose above 200°. XX (21.9 g.) and 41.9 g. PCl5 heated 3 hrs. at 170-80°, cooled, diluted with 150 cc. dry C6H6, filtered, evaporated, the residual brown oil in 100 cc. di-oxane and 100 cc. H2O cooled, treated dropwise with stirring with 150 cc. concentrated NH4OH, stirred 2 hrs., diluted with 200 cc. H2O, acidified with concentrated HCl, filtered, and the precipitate reprecipitated from dilute aqueous NaOH with concentrated HCl 51% 2-amino-3-nitro-5-pyridinesulfonamide, yellow platelets, m. 287-9° (decomposition), which, reduced in the usual manner gave 61% 3-NH2 analog HCl salt (XXII), m. 231-2° (decomposition) (MeOH). XXII (2.5 g.) refluxed 2 hrs., with 50 cc. HC(OEt)3 and cooled gave 83% imidazo[b]pyridine-6-sulfonamide, m. 289-90° (H2O). 2,6-Diamino-3-nitrosopyridine in H2O hydrogenated over Pt, filtered into concentrated HCl, and evaporated in vacuo 84% 2,3,6-triaminopyridine (XXIII).2HCl, m. 270-1° (H2O); the solution from a similar hydrogenation filtered into concentrated H2SO4 gave the sulfate of XXIII, m. 242-3° (decomposition). XXIII.2HCl (9.85 g.) refluxed 8 hrs. with 75 cc. 98-100% HCO2H, evaporated in vacuo and the oily residue dissolved in 50 cc. 2N H2SO4, refluxed 0.5 hr., and diluted with 50 cc. MeOH and excess Et2O precipitated 72% bis(5-aminoimidazo[b]pyridine)sulfate (XXIV), m. 259-60° (decomposition) (aqueous EtOH). XXIV (7.32 g.) in 150 cc. H2O containing 5 cc. concentrated H2SO4 treated at 5-10° with 2.76 g. NaNO2 in 25 cc. H2O with stirring, stirred 2 hrs., neutralized with 2N NaOH, and filtered gave 37% 5-hydroxyimidazo[b]pyridine, m. 311-13° (decomposition). XXIII sulfate (11.1 g.), 100 cc. H2O, and 50 cc. concentrated HCl treated at 5-10° with 13.8 g. NaNO2 in 75 cc. H2O and processed in the usual manner gave 16% 5-hydroxypyrido[2,3-d]-v-triazole, m. 280-2° (decomposition). 4-Aminopyridine (47 g.) added gradually below 10° to 200 cc. cold concentrated H2SO4, treated dropwise during 0.5 hr. with 27 cc. fuming HNO3, warmed during about 1 hr. to room temperature, treated with stirring with 27 cc. fuming HNO3 at 85-90° during 0.5 hr., stirred until room temperature was reached, poured onto 1 kg. crushed ice, neutralized partially with 40% aqueous NaOH, filtered, the filtrate basified strongly with concentrated NH4OH, filtered, and the combined filter cakes (60-5%) recrystallized from H2O gave 4-amino-3,5-dinitropyridine (XXV), bright yellow plates, m. 168-9°. XXV (36.8 g.) added gradually with stirring to 200 cc. 2 NH4OH previously saturated at 0-5° with H2S, stirred 1 hr., and filtered yielded 47% di-NH2 analog (XXVI) of XXV, ruby-red needles, m. 239° (H2O), converted by the method described for XI in quant. yields to 7-nitroimidazo[c]pyridine (XXVIa), m. 275-6°, and to 7-nitropyrido[3,4-d]-v-triazole (XXVII), m. 266-8° (decomposition). XXVI in EtOH hydrogenated over Pt and filtered into concentrated HCl gave 3,4,5-triaminopyridine (XXVIII).3HCl, m. 275-8° (decomposition). Similarly was prepared XXVIII.2H2SO4, m. 252-3° (decomposition), in 100% yield. XXVIII.2H2SO4 (6.4 g.) in 50 cc. 98-100% HCO2H refluxed 4 hrs., evaporated, the residual oil refluxed 0.5 hr. with 50 cc. 2N H2SO4, and the solution concentrated to half the original volume and diluted with 100 cc. MeOH and excess Et2O gave 7-aminoimidazo[c]pyridine sulfate, m. 240-1° (decomposition), also obtained from XXVIa with SnCl2 and HCl. XXVII (6.25 g.) added gradually to 30 g. SnCl2 in 100 cc. concentrated HCl, heated 0.5 hr. on the steam bath, cooled, filtered, the residue decomposed in 0.3N HCl with H2S, filtered, the filtrate evaporated, and the residue dissolved in 50 cc. 2N NaOH, refluxed 0.5 hr., and partially neutralized with HCl precipitated 38% 7-NH2 analog of XXVII, decompose above 300° (H2O). XX (21.9 g.) and 41.9 g. PCl5 heated to solution at 178-80°, then 2 hrs. longer, cooled, mixed with 150 cc. C6H6, filtered, the filtrate evaporated in vacuo, the residual brown oil added gradually with stirring and cooling, to 152 g. SnCl2 in 300 cc. concentrated HCl, heated 1 hr. on the steam bath, cooled, filtered, a 5-g. portion of the residue (34 g.) treated at 5-10° in 50 cc. 2N HCl with 1.38 g. NaNO2 in 25 cc. H2O with stirring, the mixture stirred 2 hrs., and the red precipitate recrystallized from aqueous HCONMe2 81% 6-mercaptopyrido[2,3-d]-v-triazole, m. 234-5° (decomposition). XI debrominated in the usual manner by hydrogenation yielded 71% 5-methylpyrido[2,3-d]-v-triazole, m. 249-51° (decomposition). XII was converted similarly in quant. yield to 5-methylpyrido[2,3-d]-v-triazole, m. 219-20°.

Journal of the American Chemical Society published new progress about Metabolism, animal. 92276-38-5 belongs to class triazoles, and the molecular formula is C5H3BrN4, Application of C5H3BrN4.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Avila, Luis; Elguero, Jose; Julia, Sebastian; Del Mazo, Jose M. published the artcile< N-Polyazolylmethanes. IV. Reaction of benzotriazole with methylene chloride and chloroform under phase transfer conditions>, Formula: C19H13N9, the main research area is benzotriazole condensation chloroform dichloromethane; methylenebisbenzotriazole; methylidynetrisbenzotriazole.

Six of 7 possible products of the reaction of benzotriazole (I) with CH2Cl2 and CHCl3 under phase-transfer conditions were isolated and characterized by 1H and 13C NMR and mass spectra. The relative amounts of the products follow an (a + b)n relationship (n = 2, 3), where a and b represent the relative contribution of I tautomeric forms.

Heterocycles published new progress about Condensation reaction. 88088-95-3 belongs to class triazoles, and the molecular formula is C19H13N9, Formula: C19H13N9.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Timmis, G. M.; Epstein, S. S. published the artcile< New antimetabolites of vitamin B12>, Electric Literature of 92276-38-5, the main research area is ANTIMETABOLITES/pharmacology; VITAMIN B 12/antagonists.

Of some 100 compounds tested as inhibitors of vitamin B12 in a microbiol. system using Euglena gracilis var. z as the test organism, the following possessed antimetabolite activity: 4-nitro-6-chlorobenzimidazole, 5,6-dichlorobenzimidazole, 4,5,6-trichlorobenzimidazole, 5-bromo-2,7-diazabenzimidazole, purine, purine riboside, and 5-fluorouracil. Seven others, while inhibitory, were not antimetabolites.

Nature (London, United Kingdom) published new progress about 92276-38-5. 92276-38-5 belongs to class triazoles, and the molecular formula is C5H3BrN4, Electric Literature of 92276-38-5.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Katritzky, Alan R.; Wu, Hong; Xie, Linghong published the artcile< Novel Tele nucleophilic aromatic substitutions in α-(benzotriazol-1-yl)alkyl aryl ketones>, Synthetic Route of 88088-95-3, the main research area is nucleophilic aromatic substitution benzotriazolylalkyl aryl ketone; tele nucleophilic aromatic substitution benzotriazolylalkyl ketone.

Reactions of α-(benzotriazol-1-yl)alkyl aryl ketones with alkyllithiums or Grignard reagents afforded para-alkylated products via novel tele nucleophilic aromatic substitutions.

Tetrahedron Letters published new progress about Ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 88088-95-3 belongs to class triazoles, and the molecular formula is C19H13N9, Synthetic Route of 88088-95-3.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Katritzky, Alan R.; Yang, Zhijun; Lam, Jamshed N. published the artcile< Tris(benzotriazol-1-yl)methane: a -CO2H synthon for the preparation of carboxylic acid>, Formula: C19H13N9, the main research area is benzotriazolylmethane carboxylic acid synthon; synthon carboxylic acid trisbenzotriazolylmethane; carboxylic acid synthon trisbenzotriazolylmethane.

Lithiation of tris(benzotriazol-1-yl)methane (I) gives the carbanion, which gave substitution products with electrophiles. Acidic hydrolysis of the products gave carboxylic acids in good yields. Thus, lithiated I and PhCH2Br gave a substitution product, which on hydrolysis gave PhCH2CO2H in 92% yield. Several α-functionalized carboxylic acids were prepared by this method.

Synthesis published new progress about Carboxylic acids Role: SPN (Synthetic Preparation), PREP (Preparation). 88088-95-3 belongs to class triazoles, and the molecular formula is C19H13N9, Formula: C19H13N9.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Guedira, F.; Ouijja, N.; Zaydoun, S.; Komiha, N.; Lautie, A.; Idrissi, M. Saidi published the artcile< Vibrational and theoretical study of the protonation of 3,4'-bi-1,2,4-triazole and its C-brominated and C-methylated derivatives>, Electric Literature of 389122-08-1, the main research area is bitriazole protonation vibrational spectra exptl theor; bromo derivative bitriazole protonation vibrational spectra exptl theor; methyl derivative bitriazole protonation vibrational spectra exptl theor.

An approach to determine the structure of protonated 3,4′-di-1,2,4-triazoles was carried out using the semi-empirical M.N.D.O. (MNDO) method. The results obtained for 3,4′-di-1,2,4-triazole show that the isolated state of the N1H form has great stability, and indicated that its protonation mainly occurs on one of the pyridine type N of the 4-triazolyl group. The vibration spectra of the di-1,2,4-triazolium, 5-methyl-di-1,2,4-triazolium and 5-bromo-di-1,2,4-triazolium chlorides were studied between 4000 and 200 cm-1. An attribution of the fundamental modes is proposed, and the effect of protonation on the normal vibration frequencies is discussed. Using these spectroscopic results, the strength and type of H bonds existing in the crystal could be assessed and a mol. structure proposed.

Canadian Journal of Analytical Sciences and Spectroscopy published new progress about Chemical chains. 389122-08-1 belongs to class triazoles, and the molecular formula is C2H3BrN4, Electric Literature of 389122-08-1.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Schulze, Volker K.; Klar, Ulrich; Kosemund, Dirk; Wengner, Antje M.; Siemeister, Gerhard; Stoeckigt, Detlef; Neuhaus, Roland; Lienau, Philip; Bader, Benjamin; Prechtl, Stefan; Holton, Simon J.; Briem, Hans; Marquardt, Tobias; Schirok, Hartmut; Jautelat, Rolf; Bohlmann, Rolf; Nguyen, Duy; Fernandez-Montalvan, Amaury E.; Boemer, Ulf; Eberspaecher, Uwe; Bruening, Michael; Doehr, Olaf; Raschke, Marian; Kreft, Bertolt; Mumberg, Dominik; Ziegelbauer, Karl; Brands, Michael; von Nussbaum, Franz; Koppitz, Marcus published the artcile< Treating Cancer by Spindle Assembly Checkpoint Abrogation: Discovery of Two Clinical Candidates, BAY 1161909 and BAY 1217389, Targeting MPS1 Kinase>, Recommanded Product: 6-Chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine, the main research area is cancer treatment MPS1 inhibitors HTS hits ATP binding site.

Inhibition of monopolar spindle 1 (MPS1) kinase represents a novel approach to cancer treatment: instead of arresting the cell cycle in tumor cells, cells are driven into mitosis irresp. of DNA damage and unattached/misattached chromosomes, resulting in aneuploidy and cell death. Starting points for our optimization efforts with the goal to identify MPS1 inhibitors were two HTS hits from the distinct chem. series “”triazolopyridines”” and “”imidazopyrazines””. The major initial issue of the triazolopyridine series was the moderate potency of the HTS hits. The imidazopyrazine series displayed more than 10-fold higher potencies; however, in the early project phase, this series suffered from poor metabolic stability. Here, we outline the evolution of the two hit series to clin. candidates BAY 1161909 (I) and BAY 1217389 (II), and reveal how both clin. candidates bind to the ATP site of MPS1 kinase, while addressing different pockets utilizing different binding interactions, along with their synthesis and preclin. characterization in selected in vivo efficacy models.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 1239647-60-9 belongs to class triazoles, and the molecular formula is C6H5ClN4, Recommanded Product: 6-Chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine.

Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics