120739-67-5Relevant articles and documents
Picolyl alkyl amines as novel tyrosinase inhibitors: Influence of hydrophobicity and substitution
Bandyopadhyay, Punam,Jha, Sujeetkumar,Imran Ali
, p. 9780 - 9786 (2009)
Several novel picolyl alkyl amine derivatives (A-L) were synthesized, and the influence of hydrophobicity and substitution on the inhibition of mushroom tyrosinase toward both monophenolase and dlphenolase activities are described, α-, β-, and γ-picolyl amines are neither the substrates nor the inhibitors; however, the inhibition Is induced by the incorporation of an alkyl chain. The inhibition was strongly dependent on the substitution on a pyridine ring, and the inhibition follows the trend of a-picolyl alkyl amines (A, D, G) β-picolyl alkyl amines (B, E, H) γ -picolyl alkyl amines (C, F, I). The inhibition kinetics have been investigated, and γ-substituted derivatives were found to be a mixed type of inhibitor, whereas β-substituted derivatives were found to exhibit uncompetitive inhibition toward the oxidation of L-DOPA.
Mixed carboxylic-sulfonic anhydride in reaction with imines: A straightforward route to water-soluble β-lactams via a Staudinger-type reaction
Bakulina, Olga,Dar'In, Dmitry,Krasavin, Mikhail
, p. 3989 - 3998 (2018/06/08)
The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.
Direct aziridination of nitroalkenes affording N-alkyl-C-nitroaziridines and the subsequent Lewis acid mediated isomerization to β-nitroenamines
Hao, Feiyue,Asahara, Haruyasu,Nishiwaki, Nagatoshi
, p. 5442 - 5445 (2017/11/06)
A mild and highly diastereoselective one-pot synthesis of trans-N-alkyl-C-nitroaziridines was achieved by treatment of nitroalkenes with aliphatic amines and N-chlorosuccinimide. Treatment of the obtained aziridines with a Lewis acid resulted in a facile ring opening reaction, accompanied by rearrangement and isomerization into functionalized (Z)-β-nitroenamines.
New Heterocyclic Product Space for the Castagnoli-Cushman Three-Component Reaction
Dar'In, Dmitry,Bakulina, Olga,Chizhova, Maria,Krasavin, Mikhail
supporting information, p. 3930 - 3933 (2015/08/18)
Significant expansion of heterocyclic product space accessible by the Castagnoli-Cushman reaction (CCR) has been achieved via the use of glutaric anhydride analogues containing endocyclic substitutions with oxygen, nitrogen, and sulfur. Incorporation of these heteroatoms in the anhydride's backbone results in enhanced reactivity and generally lower temperatures that are required for the reactions to go to completion. These findings are particularly significant in light of the CCR recently recognized as an efficient tool for lead-oriented synthesis.
Synthesis and evaluation of diphenylphosphinic amides and diphenylphosphine oxides as inhibitors of Kv1.5
Olsson, Roine I.,Jacobson, Ingemar,Bostroem, Jonas,Fex, Tomas,Bjoere, Annika,Olsson, Christina,Sundell, Johan,Gran, Ulrik,Oehrn, Anna,Nordin, Andreas,Gyll, Jonna,Thorstensson, Maria,Hayen, Ahlke,Aplander, Karolina,Hidestal, Olle,Jiang, Fanyi,Linhardt, Gunilla,Forsstroem, Elin,Collins, Teresa,Sundqvist, Monika,Lindhardt, Emma,Astrand, Annika,Loefberg, Boel
, p. 706 - 710 (2013/02/23)
Diphenylphosphinic amides and diphenylphosphine oxides have been synthesized and tested as inhibitors of the Kv1.5 potassium ion channel as a possible treatment for atrial fibrillation. In vitro structure-activity relationships are discussed and several compounds with Kv1.5 IC50 values of a rabbit PD-model are included.
Application of bis(trimethylsilyl) phosphonite in the efficient preparation of new heterocyclic -aminomethyl- H -phosphinic acids
Olszewski, Tomasz K.,Boduszek, Bogdan
experimental part, p. 437 - 442 (2011/04/22)
A simple, reproducible, and efficient preparation of new heterocyclic -aminomethyl-H-phosphinic acids is reported. The synthetic protocol is based on the application of bis(trimethylsilyl) phosphonite, as an efficient phosphorous nucleophile, in the reaction with the corresponding heterocyclic imines. Subsequent methanolysis of the addition intermediates leads to the expected heterocyclic -aminomethyl-H-phosphinic acids in fair to good yields. Additionally, acidic hydrolysis of benzhydrylamino derivatives allows the efficient preparation of free -aminomethyl-H-phosphinic acids in good yields and high purity after simple crystallization. Georg Thieme Verlag Stuttgart New York.
