Month: November 2022

Takeuchi, Tomoki published the artcileDiscovery of Aryloxyphenyl-Heptapeptide Hybrids as Potent and Selective Matrix Metalloproteinase-2 Inhibitors for the Treatment of Idiopathic Pulmonary Fibrosis, Computed Properties of 71989-31-6, the publication is Journal of Medicinal Chemistry (2022), 65(12), 8493-8510, database is CAplus and MEDLINE.

Matrix metalloproteinase-2 (MMP2) is a zinc-dependent endopeptidase that plays important roles in the degradation of extracellular matrix proteins. MMP2 is considered to be an attractive target for the treatment of various diseases such as cancer, arthritis, and fibrosis. In this study, we have developed a novel class of MMP2-selective inhibitors by hybridizing the peptide that binds to a zinc ion and S2-S5 pockets with small mols. that bind to the S1′ pocket. Structural modifications based on X-ray crystallog. revealed that the introduction of 2,4-diaminobutanoic acid (Dab) at position 4 dramatically enhanced MMP2 selectivity by forming an electrostatic interaction with Glu130. After improving the metabolic and chem. stability, TP0556351 (9)(I) was identified. It exhibited potent MMP2 inhibitory activity (IC₅₀ = 0.20 nM) and extremely high selectivity. It suppressed the accumulation of collagen in a bleomycin-induced idiopathic pulmonary fibrosis model in mice, demonstrating the efficacy of MMP2-selective inhibitors for fibrosis.

Journal of Medicinal Chemistry published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C38H74Cl2N2O4, Computed Properties of 71989-31-6.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kaga, Atsushi published the artcileNucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite, Safety of N1,N2-Dibenzylethane-1,2-diamine, the publication is Angewandte Chemie, International Edition (2017), 56(39), 11807-11811, database is CAplus and MEDLINE.

A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.

Angewandte Chemie, International Edition published new progress about 140-28-3. 140-28-3 belongs to catalysis-chemistry, auxiliary class Benzenes, name is N1,N2-Dibenzylethane-1,2-diamine, and the molecular formula is C16H20N2, Safety of N1,N2-Dibenzylethane-1,2-diamine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Nishida, Masakazu published the artcileFormation of perfluorinated polyphenylenes by multiple pentafluorophenylation using C₆F₅Si(CH₃)₃, Synthetic Route of 1206-46-8, the publication is Journal of Fluorine Chemistry (2010), 131(12), 1314-1321, database is CAplus.

Pentafluorophenylation of perfluoroarenes with C₆F₅Si(CH₃)₃ was investigated by using NMR and MALDI-TOF-MS techniques. Successive multiple pentafluorophenylation easily occurred not only on the para-position but also on the ortho-positions to provide perfluorinated p-phenylene and m-phenylene compounds The perfluoroarenes having electron-withdrawing substituents provided oligo- to poly-(phenylene)s depending on the added amounts of C₆F₅Si(CH₃)₃, while the perfluoroarenes having electron-donor substituents gave H(C₆F₄)_nF polymers produced from C₆F₅H, which was the decomposed product of C₆F₅Si(CH₃)₃.

Journal of Fluorine Chemistry published new progress about 1206-46-8. 1206-46-8 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Trimethyl(perfluorophenyl)silane, and the molecular formula is C9H9F5Si, Synthetic Route of 1206-46-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Kitagawa, Motoji published the artcilePancreatic and biliary excretion of camostat in dogs, COA of Formula: C17H19N3O7S, the publication is Digestion (1988), 39(4), 204-9, database is CAplus and MEDLINE.

To confirm whether camostat (Foy-305) is excreted into bile or pancreatic juice, camostat (5 mg/kg/h) was given i.v. to dogs with pancreatic or biliary fistulae. Camostat and its active metabolite (Foy-251) (I) in bile and pancreatic juice were measured by HPLC and by their trypsin-inhibitory activity. Camostat did not alter the exocrine pancreatic secretion of fluid, bicarbonate, protein or trypsin stimulated by secretin and caerulein. Camostat and its active metabolite were detected in bile by HPLC and trypsin-inhibitory activity (the mean excretion rate was 1.3% of the i.v. dose of camostat), but they were not detectable in pancreatic juice. In conclusion, camostat and its active metabolite were excreted into bile but not into pancreatic juice.

Digestion published new progress about 71079-09-9. 71079-09-9 belongs to catalysis-chemistry, auxiliary class Salt,Carboxylic acid,Carbamidine,Amine,Benzene,Ester,Protease,Ser/Thr Protease, name is 2-(4-((4-Guanidinobenzoyl)oxy)phenyl)acetic acid methanesulfonic acid salt, and the molecular formula is C17H19N3O7S, COA of Formula: C17H19N3O7S.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Marling, J. B. published the artcileLasing characteristics of seventeen visible-wavelength dyes using a coaxial-flashlamp-pumped laser, Product Details of C18H15N3O3, the publication is Applied Optics (1974), 13(10), 2317-20, database is CAplus and MEDLINE.

The performance and tuning characteristic of organic dye lasers were measured using com. available coaxial flashlamps as the pumping source. Tuning by a diffraction grating permitted continuous coverage of the 4200-7500-? region at up to 0.6% tuned output energy efficiency. Preliminary results with a 600-J Marx-Bank coaxial laser at 4500 ? show 1% efficiency and single-pass unsaturated gain >20 at 4500 ?.

Applied Optics published new progress about 10510-54-0. 10510-54-0 belongs to catalysis-chemistry, auxiliary class Other Aromatic Heterocyclic,Salt,Amine,Inhibitor,Inhibitor, name is 5,9-Diaminobenzo[a]phenoxazin-7-ium acetate, and the molecular formula is C18H15N3O3, Product Details of C18H15N3O3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Laufer, Stefan published the artcileTri- and tetra-substituted imidazoles as p38¦Á mitogen-activated protein kinase inhibitors, Application of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(22), 6671-6675, database is CAplus and MEDLINE.

The synthesis of 2,4,5-tri-substituted and 1,2,4,5-tetra-substituted imidazoles, e.g. I, as potent p38¦Á mitogen-activated protein kinase inhibitors is described. The tri-substituted imidazole series was found to be more potent than the tetra-substituted imidazole series. Many of these compounds show low-nanomolar activities in the isolated p38¦Á MAP kinase inhibition assay. The structure-activity relationships between these two series are different and not comparable.

Bioorganic & Medicinal Chemistry Letters published new progress about 16909-09-4. 16909-09-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Benzene,Ether, name is (E)-3-(2,4-Dimethoxyphenyl)acrylic acid, and the molecular formula is C11H12O4, Application of (E)-3-(2,4-Dimethoxyphenyl)acrylic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Nguyen, Vu T. published the artcilePhotocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides, Name: 3-Benzoylpropionicacid, the publication is Chemical Science (2021), 12(18), 6429-6436, database is CAplus and MEDLINE.

A visible light-induced, dual catalytic platform that for the first time allows for a one-step access to sulfonamides RS(O)₂R¹ (R = 4,4-dimethylcyclohexyl, heptadecyl, 4-oxo-4-phenylbutyl, etc.; R¹ = 2,3-dihydro-1H-indol-1-yl, (3,4,5-trimethylphenyl)aminyl, morpholin-4-yl, etc.) and sulfonyl azides R²S(O)₂N₃ (R² = 5-methoxy-5-oxopentyl, 4-(5-methylthiophen-2-yl)-4-oxobutyl, oxan-4-yl, etc.) directly from carboxylic acids R/R²COOH was reported. The broad scope of the direct decarboxylative amidosulfonation (DDAS) platform is enabled by the efficient direct conversion of carboxylic acids to sulfinic acids that are catalyzed by acridine photocatalysts and interfaced with copper-catalyzed sulfur-nitrogen bond-forming cross-couplings with both electrophilic and nucleophilic reagents.

Chemical Science published new progress about 2051-95-8. 2051-95-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ketone, name is 3-Benzoylpropionicacid, and the molecular formula is C10H10O3, Name: 3-Benzoylpropionicacid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Masui, Yoichi published the artcileReversible Generation of Labile Secondary Carbocations from Alcohols in the Nanospace of H-Mordenite and Their Long-Lasting Preservation at Ambient Temperature, Product Details of C13H10F2, the publication is Journal of the American Chemical Society (2017), 139(25), 8612-8620, database is CAplus and MEDLINE.

Secondary carbocations are rarely observed spectrometrically for prolonged durations at ambient temperatures because of their instability. In this study, when 4,4′-difluorobenzhydrol (1) was mixed with H-mordenite (H-Mor), the 4,4′-difluorodiphenylmethyl cation (2) was generated as the main product, identified by UV-vis and ¹³C-MAS NMR spectroscopies, and was preserved for over 1 wk at ambient temperature Surprisingly, the polymerization and disproportionation of 1 barely proceeded within the micropores of H-Mor. However, these side reactions prevailed in TfOH and formation of 2 was not observed Preservation of other secondary carbocations from benzhydrol, 4,4′-dichlorobenzhydrol, and 9-fluorenol was also realized in H-Mor. It was confirmed that the generation of 2 from 1 was controlled by thermodn. equilibrium rather than kinetic regulations. The equilibrium between 2 and 1 was accompanied by reversible chromism, which could be easily controlled by altering the moisture content in H-Mor. Moreover, novel insights into specific acid catalysis in zeolites densely populated with acid sites on the inner surface of micropores are described herein.

Journal of the American Chemical Society published new progress about 457-68-1. 457-68-1 belongs to catalysis-chemistry, auxiliary class Fluoride,Benzene, name is Bis(4-fluorophenyl)methane, and the molecular formula is C13H10F2, Product Details of C13H10F2.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Nakamura, Ryuji published the artcileOral camostat mesilate administration on alkaline reflux esophagitis in an experimental animal model, Synthetic Route of 71079-09-9, the publication is Iwate Igaku Zasshi (1999), 50(Suppl.), 653-659, database is CAplus.

Following total gastrectomy and esophagojejunostomy in an end-to-side fashion, tabs of a synthetic proteinase inhibitor, camostat mesilate, were fed to 15 dogs via cervical esophagostomy. A 67% decrease in trypsin activity was observed in duodenal juice aspirated 30 min after administration. The suppression lasted 90 min. Administration of camostat 3 times per day for 2 wk (n = 5) failed to significantly improve erosive esophagitis noted by esophagoscopy, although a tendency of hemostasis of hemorrhagic erosion has been induced. In postoperative alk. reflux esophagitis, oral camostat administration alone is insufficient to protect the esophageal mucosa. Bile acid or other constituents of reflux must also be neutralized to improve the clin. condition.

Iwate Igaku Zasshi published new progress about 71079-09-9. 71079-09-9 belongs to catalysis-chemistry, auxiliary class Salt,Carboxylic acid,Carbamidine,Amine,Benzene,Ester,Protease,Ser/Thr Protease, name is 2-(4-((4-Guanidinobenzoyl)oxy)phenyl)acetic acid methanesulfonic acid salt, and the molecular formula is C17H19N3O7S, Synthetic Route of 71079-09-9.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Fritsche, Hans published the artcileReduction of organic compounds of pentavalent phosphorus to phosphines. III. Preparation of primary and secondary phosphines with silanes, Safety of Difluorodiphenylsilane, the publication is Chemische Berichte (1965), 98(5), 1681-7, database is CAplus.

cf. CA 62, 10457d. Phosphonate esters and phosphinic acids and their esters or chlorides, as well as di- and monohalophosphines were reduced with organic silanes or Cl₃SiH (I) to primary and secondary phosphines, resp. BuP(O)(OEt)₂ (II) (77.6 g.) and 147.2 g. Ph₂SiH₂ (III) heated 3 hrs. under N at 150-200¡ã yielded 27 g. BuPH₂ (IV), b. 60¡ã. II (19.4 g.) and 43 g. methylpolysiloxane (V) heated with stirring 3 hrs. under N at 200¡ã and then 2 hrs. at 275¡ã gave 8 g. IV. All runs were performed under N. PhP(O)(OEt)₂ (21.4 g.) and 36.8 g. III heated 2 hrs. at 200¡ã gave 9.6 g. PhPH₂ (VI), b. 130-40¡ã. PhPCl₂ (35.8 g.) and 36.8 g. III gave similarly 18 g. VI. PhPCl₂ (35.8 g.), 30 g. I, and 22 g. Et₃N in 250 cc. C₆H₆ refluxed 2 hrs. and treated with 150 cc. 2% aqueous NaOH gave 12 g. VI, b₁₄ 60¡ã. Bu₂P(O)OH (26.7 g.) and 41.4 g. III heated 4 hrs. at 200¡ã yielded 16.8 g. Bu₂PH, b₁₄ 68-70¡ã. Bu₂P(O)Cl (19.65 g.) and 27.6 g. III heated 3 hrs. at 250¡ã gave 13.9 g. Bu₂PH, b₁₄ 70¡ã. Bu₂P(O)Cl (19.65 g.), 30 g. I, and 22 g. Et₃N in 250 cc. C₆H₆ refluxed 2 hrs. yielded 9.2 g. Bu₂PH, b₁₄ 70¡ã. 1-Hydroxy-1-oxo-3,4-dimethyl-2-phospholene (21.8 g.) and 41.4 g. III heated 4 hrs. at 150-90¡ã yielded 13.8 g. 3,4-dimethyl-2-phospholene, b. 146-8¡ã. 1-Hydroxy-1-oxo-3-methyl-2-phospholene with III gave similarly 78% 3-methyl-2-phospholene, b. 80¡ã, and 1-hydroxy-1-oxo-2-phospholene with PhSiH₃ gave 73% 2-phospholene, b. 75¡ã. 10-Hydroxy-10-oxo-2,8-dimethylphenoxaphosphine (73 g.) and 84 g. III heated 3 hrs. at 250¡ã gave 54.2 g. 2,8-dimethylphenoxaphosphine, air-sensitive crystals, m. 56¡ã (under N). Ph₂P(O)(OMe) (34.8 g.) and 41.4 g. III heated 4 hrs. at 190¡ã yielded 16.8 g. Ph₂PH, b_0.35 105-15¡ã. Ph₂P(O)OH (22 g.) in 100 cc. dry C₆H₆ refluxed 2 hrs. with 40.6 g. I and treated with 100 cc. 20% aqueous NaOH yielded 7.2 g. Ph₂PH, b_0.3 110¡ã. Ph₂P(O)Cl (23.6 g.) and 27.6 g. III during 3 hrs. at 200-50¡ã yielded 16.5 g. Ph₂PH, b_0.07 107¡ã. Ph₂PCl (44 g.) and 18.4 g. III during 2 hrs. at 200¡ã gave 23 g. Ph₂PH, b₁₄ 165¡ã. Ph₂PCl (22 g.), 15 g. I, and 11 g. Et₃N in 80 cc. C₆H₆ refluxed 2 hrs. and treated with 80 cc. 30% aqueous NaOH gave 14 g. Ph₂PH, b₁₂ 155¡ã. 2,4,6-Me₃C₆H₂MgBr from 80 g. 2,4,6-Me₃C₆H₂Br and 9.6 g. Mg in tetrahydrofuran treated dropwise with 30.5 g. POCl₃ in tetrahydrofuran, and the precipitate refluxed 0.5 hr. with alc. NaOEt, treated with 20% aqueous NaOH, and again refluxed 0.5 hr. yielded 32 g. (2,4,6-Me₃C₆H₂)₂P(O)OH (VII), m. 210¡ã (EtOH). VII (13 g.) and 12 g. III heated 3 hrs. at 300¡ã yielded 4 g. (2,4,6-Me₃C₆H₂)₂PH (VIII), b_0.1 140-60¡ã, m. 74¡ã (EtOH). Chloride (18.6 g.) of VII and 6.3 g. PhSiH₃ heated 10 hrs. at 150¡ã, treated with 10 cc. EtOH, and refluxed 1 hr. gave 10.3 g. VIII. (p-Me₂NC₆H₄)₂P(O)OH (30.6 g.) and 28 g. III heated 2 hrs. at 200-50¡ã gave 15 g. (p-Me₂NC₆H₄)₂PH, b_0.05 220-5¡ã, m. 137¡ã.

Chemische Berichte published new progress about 312-40-3. 312-40-3 belongs to catalysis-chemistry, auxiliary class Organic Silicones, name is Difluorodiphenylsilane, and the molecular formula is C12H10F2Si, Safety of Difluorodiphenylsilane.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia