875537-66-9Relevant academic research and scientific papers
Hypothesis-Driven, Structure-Based Design in Photopharmacology: The Case of eDHFR Inhibitors
Kobauri, Piermichele,Galenkamp, Nicole S.,Schulte, Albert M.,De Vries, Jisk,Simeth, Nadja A.,Maglia, Giovanni,Thallmair, Sebastian,Kolarski, Du?an,Szymanski, Wiktor,Feringa, Ben L.
, p. 4798 - 4817 (2022/03/27)
Photopharmacology uses light to regulate the biological activity of drugs. This precise control is obtained through the incorporation of molecular photoswitches into bioactive molecules. A major challenge for photopharmacology is the rational design of photoswitchable drugs that show light-induced activation. Computer-aided drug design is an attractive approach toward more effective, targeted design. Herein, we critically evaluated different structure-based approaches for photopharmacology with Escherichia coli dihydrofolate reductase (eDHFR) as a case study. Through the iterative examination of our hypotheses, we progressively tuned the design of azobenzene-based, photoswitchable eDHFR inhibitors in five design-make-switch-test-analyze cycles. Targeting a hydrophobic subpocket of the enzyme and a specific salt bridge only with the thermally metastable cis-isomer emerged as the most promising design strategy. We identified three inhibitors that could be activated upon irradiation and reached potencies in the low-nanomolar range. Above all, this systematic study provided valuable insights for future endeavors toward rational photopharmacology.
Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst
Huang, Lei,Qiu, Shiqin,Wei, Yongge,Xie, Jingyan,Yu, Han,Zeng, Xianghua,Zhao, Weizhe
supporting information, p. 7677 - 7680 (2021/08/09)
We report an efficient method for the oxidative dehydrogenation of hydrazines and diarylamines in aqueous ethanol using Anderson-type polyoxomolybdate-based iron(iii) as a catalyst and hydrogen peroxide as an oxidant. A series of azo compounds and tetraarylhydrazines were obtained in moderate to excellent yields. The reaction conditions and substrate scopes are complementary or superior to those of more established protocols. In addition, the catalyst shows good stability and reusability in water. The preliminary mechanistic studies suggest that a radical process is involved in the reaction.
First use of p-tert-butylcalix[4]arene-tetra-O-acetate as a nanoreactor having tunable selectivity towards cross azo-compounds by trapping silver ions
Sarkar, Piyali,Mukhopadhyay, Chhanda
supporting information, p. 442 - 451 (2016/01/30)
p-tert-Butylcalix[4]arene-tetra-O-acetate was established for the first time as a member of the nanoreactor series, even without having any -OH group. The nano range distribution of this nanoreactor was ascertained by DLS, SEM and TEM studies. The capability of this cavitand towards hosting amines in a competitive manner generates a new green pathway for cross coupling of aromatic amines to give the corresponding azo-compounds. In this context, using p-tert-butylcalix[4]arene-tetra-O-acetate as a nanoreactor and silver nitrate as a catalyst, we got the cross azo-compound in good to excellent yields in the eco-friendly solvent water. This green methodology is also applicable for the synthesis of respective homo-compounds.
A practical synthesis of azobenzenes through oxidative dimerization of aromatic amines using tert-butyl hypoiodite
Takeda, Youhei,Okumura, Sota,Minakata, Satoshi
supporting information, p. 1029 - 1033 (2013/05/09)
A straightforward, convenient, and efficient synthetic method of azobenzenes through oxidative dimerization of aromatic amines using a unique and cost-effective iodinating reagent is described. This new method allows for easy access to both of symmetrical and unsymmetrical azobenzenes under extremely mild conditions. Georg Thieme Verlag Stuttgart. New York.
Oxidative dimerization of (hetero)aromatic amines utilizing t-BuOI leading to (hetero)aromatic azo compounds: Scope and mechanistic studies
Okumura, Sota,Lin, Chun-Hsuan,Takeda, Youhei,Minakata, Satoshi
, p. 12090 - 12105 (2014/01/06)
A straightforward synthetic method of both symmetric and unsymmetric aromatic azo compounds through an efficient and cross-selective oxidative dimerization of aromatic amines using tert-butyl hypoiodite (t-BuOI) under metal-free and mild conditions has been developed. This method was also found applicable to the synthesis of heteroaromatic azo compounds. The spectroscopic study indicates the involvement of N,N-diiodoanilines in the oxidative reaction as the key intermediate.
Oxidative dimerization of aromatic amines using tBuOI: Entry to unsymmetric aromatic azo compounds
Takeda, Youhei,Okumura, Sota,Minakata, Satoshi
supporting information; experimental part, p. 7804 - 7808 (2012/09/05)
It's all the hype: An oxidative dimerization reaction of aromatic amines utilizing tert-butyl hypoiodite (tBuOI) under mild reaction conditions leads to aromatic azo compounds (see scheme). The method allows access to unsymmetric aromatic azo compounds, which are difficult to prepare by conventional synthetic methods, in a selective manner. Copyright
Bidentate and tetradentate β-aminovinyl trifluoromethylated ketones and their copper(II) complexes: Synthesis, characterization and redox chemistry
Chopin, Nicolas,Medebielle, Maurice,Pilet, Guillaume
experimental part, p. 1093 - 1103 (2012/04/23)
New polyfunctional bidentate and tetradentate trifluoromethylated enaminone ligands that bear redox-active and photosensitive moieties were synthesized in moderate to good yields and their coordination chemistry with copper(II) was examined. The crystal s
Cu(I) mediated one-pot synthesis of azobenzenes from bis-Boc aryl hydrazines and aryl halides
Kim, Kyu-Young,Shin, Jeong-Taek,Lee, Kang-Sang,Cho, Cheon-Gyu
, p. 117 - 120 (2007/10/03)
N,N′-bis-Boc aryl hydrazines underwent Cu(I) catalyzed couplings with aryl halides to provide N,N′-bis-Boc diaryl hydrazines. The resulting N,N′-bis-Boc diaryl hydrazines are readily oxidized to the azobenzenes in the presence of Cu(I) and a base. A prolo
