60890-09-7Relevant academic research and scientific papers
Iron(III) Chloride Mediated para-Selective C-H Functionalization: Access to C5-Chloro and C5,C7-Dichloro/Dianisyl Substituted 2-Arylbenzoxazoles
Sahoo, Kanchanbala,Panda, Niranjan
, p. 1023 - 1030 (2022/02/03)
Iron(III) chloride mediated para-selective C?H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole b
Natural Abenquines and Their Synthetic Analogues Exert Algicidal Activity against Bloom-Forming Cyanobacteria
Nain-Perez, Amalyn,Barbosa, Luiz Cláudio Almeida,Maltha, Célia Regina álvares,Forlani, Giuseppe
, p. 813 - 818 (2017/05/05)
Abenquines are natural quinones, produced by some Streptomycetes, showing the ability to inhibit cyanobacterial growth in the 1 to 100 μM range. To further elucidate their biological significance, the synthesis of several analogues (4f-h, 5a-h) allowed us to identify some steric and electronic requirements for bioactivity. Replacing the acetyl by a benzoyl group in the quinone core and also changing the amino acid moiety with ethylpyrimidinyl or ethylpyrrolidinyl groups resulted in analogues 25-fold more potent than the natural abenquines. The two most effective analogues inhibited the proliferation of five cyanobacterial strains tested, with IC50 values ranging from 0.3 to 3 μM. These compounds may be useful leads for the development of an effective strategy for the control of cyanobacterial blooms.
Natural abenquines and synthetic analogues: Preliminary exploration of their cytotoxic activity
Nain-Perez, Amalyn,Barbosa, Luiz C.A.,Rodríguez-Hernández, Diego,Kramell, Annemarie E.,Heller, Lucie,Csuk, René
, p. 1141 - 1144 (2017/06/19)
In this study, we explore the cytotoxic activity of four natural abenquines (2a–d) and fourteen synthetic analogues (2e–j and 3a–h) against a panel of six human cancer cell lines using a SRB assay. It was found that most of the compounds revealed higher levels of cytotoxic activities than naturally occurring abenquines. The analogues carrying ethylpyrrolidinyl and ethylpyrimidinyl with either an acetyl group (2?h–i) or a benzoyl group (3f–g), were the most potent against all human cancer cell lines and displayed EC50 between a range of 0.6–3.4?μM. Notably, of the compounds tested, compound 2i proved the most cytotoxic against both ovarian (A2780) and breast (MCF7) cells, showing EC50?=?0.6 and 0.8?μM respectively. Likewise, the analogues 2i, 3f and 3?g showed strong activity against cell HT29 with EC50?=?0.9?μM for these compounds.
Synthesis of amino-1,4-benzoquinones and their use in Diels - Alder approaches to the aminonaphthoquinone antibiotics
Nawrat, Christopher C.,Lewis, William,Moody, Christopher J.
, p. 7872 - 7881 (2011/12/14)
A new protocol for the synthesis of protected amino-1,4-benzoquinones by oxidation of the corresponding 2,5-dimethoxyaniline derivatives using PhI(OAc)2 or PhI- (OCOCF3)2 in water containing 2.5% methanol is reported. The process represents an improvement over previously reported methods, both in terms of yield and number of steps, and in the range of nitrogen protecting groups that it tolerates. A number of novel aminobenzoquinones were prepared and subsequently used as dienophiles in Diels - Alder reactions to (Figure presented) form building blocks for the synthesis of the aminonaphthoquinone antibiotics such as salinisporamycin.
Iodine(V) reagents in organic synthesis. Part 2. Access to complex molecular architectures via Dess-Martin periodinane-generated o-imidoquinones
Nicolaou,Sugita,Baran,Zhong
, p. 2221 - 2232 (2007/10/03)
o-Imidoquinones, a rather rare class of compounds, are prepared from anilides by the action of Dess-Martin pedodinane (DMP) and water. Their chemistry has been extensively investigated and found to lead to p-quinones and polycyclic systems of diverse mole
