2072-30-2Relevant articles and documents
First total synthesis and phytotoxic activity of Streptomyces sp. metabolites abenquines
Nain-Perez, Amalyn,Barbosa, Luiz C.A.,Maltha, Celia R.A.,Forlani, Giuseppe
, p. 1811 - 1814 (2016/04/05)
The first total synthesis of abenquines A, B2, C and D has been achieved in three steps starting from commercially available 2,5-dimethoxyaniline, with overall yields of 41-61%. Four analogues bearing the amino acids d-valine (17), l-methionine (18), and glycine (19), and benzylamine (20), were also prepared in 45-72% yield. The inhibitory properties of these compounds were evaluated against the photoautotrophic growth of a model Synechococcus sp. strain. Abenquine C and its enantiomer were substantially ineffective, whereas all other abenquines significantly inhibited cell proliferation, with concentrations causing 50%-inhibition of algal growth ranging from 10-5 to 10-6 M.
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.
Synthesis of 9-methyl-1H-[1,4]thiazino[3,2-g]quinoline-2,5,10(3H)-trione, the B,C,D ring core of the shermilamine alkaloids
Townsend, Norman O.,Jackson, Yvette A.
, p. 3557 - 3563 (2007/10/03)
The synthesis of 9-methyl-1H-[1,4]thiazino[3,2-g]quinoline-2,5,10(3H)-trione(4), from N-(4-bromo-2,5-dimethoxyphenyl)acetamide was discussed. Oxidative cyclisation of 2,2′-disulfanediylbis[N-2,5-dimethoxyphenyl)acetamide] to 5,8-dimethoxy-2H-1,4-benzothiazin-3(4H)-one(7b) was reported. It was found that the reaction proceeded through the disulfide and iodine acted as an oxidizing agent, enabling the cyclization.
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
Acetamidoquinone and acetamidohydroxy derivatives as inhibitors for both dihydroxyacetamido epoxidase and dehydrogenase
Whiteley, Chris G.
, p. 1221 - 1227 (2007/10/03)
A series of monohydroxy and dihydroxyacetanilides, acetamidoquinones and bromoacetamidoquinones have been synthesised and tested as substrates and/or inhibitors of highly purified dihydroxyacetamido epoxidase (DHAE) and dihydroxy acetamido dehydrogenase (DHADH) from Streptomyces LL-C10337. None was found to act as substrates but many selectively inhibit the enzymes. Kinetic analysis has shown that all the compounds act as reversible competitive inhibitors with respect to the substrates 2,5-dihydroxyacetanilide and 2,3-epoxy-1,4-benzoquinone-5-acetanilide. Monohydroxy acetanilides showed weak inhibition to these enzymes compared to the dihydroxy derivatives while the more powerful inhibitors were the benzoquinoneacetanilide and its 5-bromo equivalent.
OXIDATION OF AROMATIC BIS-AMIDES BY TALLIUM (III) TRIFLUOROACETATE
Lau, K. S. Y.,Basiulis, D. I.
, p. 1175 - 1178 (2007/10/02)
Aromatic 1,2-bisamides undergo thallium (III) promoted oxidative intramolecular cyclization to generate new 5-membered heterocyclic rings.Formation of para-quinone was shown to be a minor pathway in one case.
