References
- Kempen I, Hemmer M, Counerotte S, et al. 6-Substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives in a new approach of the treatment of cancer cell invasion and metastasis. Eur J Med Chem 2008;43:2735–50
- Radanyi C, Le Bras G, Marsaud V, et al. Antiproliferative and apoptotic activities of tosylcyclonovobiocic acids as potent heat shock protein 90 inhibitors in human cancer cells. Cancer Lett 2009;274:88–94
- Nawrot-Modranka J, Nawrot E, Graczyk J. In vivo antitumor, in vitro antibacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone. Eur J Med Chem 2006;41:1301–9
- Kucherenko A, Flavin MT, Boulanger WA, et al. Novel approach for synthesis of (±)-calanolide A and its anti-HIV activity. Tetrahedron Lett 1995;36:5475–8
- Chenera B, West ML, Finkelstein JA, Dreyer GB. Total synthesis of (±)-calanolide A, a non-nucleoside inhibitor of HIV-1 reverse transcriptase. J Org Chem 1993;58:5605–6
- Žalubovskis R. In a search for selective inhibitors of carbonic anhydrases: coumarin and its bioisosteres–synthesis and derivatization. Chem Heterocycl Comp 2015;7:607–12
- Maresca A, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2009;53:335–44
- Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–62
- Kempen I, Papapostolou D, Thierry N, et al. 3-Bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo. Br J Cancer 2003;88:1111–18
- Zhou X, Chen Y-D, Wang T, et al. Rational design, synthesis, biological evaluation, homology and docking studies of coumarin derivatives as α1-adrenoceptor antagonists. Chem Biodiversity 2011;8:1052–64
- Tyagi YK, Tyagi S, Raj HG, Gupta RK. Synthesis of novel 4-methylcoumarins and comparative specificities of substituted derivatives for acetoxy drug: protein transacetylase. Sci Pharm 2008;76:395–414
- Amian A, Rodriguez JN, Muniz R, et al. Treatment with oral anticoagulants (acenocoumarol): influence of the initial doses in the incidence of hemorrhagic and thromboembolic episodes. Sangre (Barc) 1994;39:413–16
- Hollick JJ, Rigoreau LJM, Cano-Soumillac C, et al. Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the Ataxia Telangiectasia mutated kinase. J Med Chem 2007;50:1958–72
- Andrs M, Korabecny J, Jun D, et al. Phosphatidylinositol 3-kinase (PI3K) and phosphatidylinositol 3-kinase-related kinase (PIKK) inhibitors: importance of the morpholine ring. J Med Chem 2015;58:41–71
- Pritchard KM, Al-Rawi J, Bradley C. Synthesis, identification and antiplatelet evaluation of 2-morpholino substituted benzoxazines. Eur J Med Chem 2007;42:1200–10
- Ihmaid SK, Al-Rawi JMA, Bradley CJ, et al. Synthesis, DNA-PK inhibition, antiplatelet activity studies of 2-(N-substituted-3-aminopyridine)-substituted-1,3-benzoxazines and DNA-PK and PI3K inhibition, homology modeling studies of 2-morpholino-(7,8-di and 8-substituted)-1,3-benzoxazines. Eur J Med Chem 2012;57:85–101
- Ihmaid S, Al-Rawi J, Bradley C, et al. Synthesis, structural elucidation, DNA-PK inhibition, homology modelling and anti-platelet activity of morpholino-substituted-1,3-naphth-oxazines. Bioorg Med Chem 2011;19:3983–94
- Ihmaid S, Al-Rawi J, Bradley C. Synthesis, structural elucidation and DNA-dependent protein kinase and antiplatelet studies of 2-amino-[5, 6, 7, 8-mono and 7, 8-di-substituted]-1,3-benzoxazines. Eur J Med Chem 2010;45:4934–46
- Morrison R, Belz T, Ihmaid SK, et al. Dual and/or selective DNA-PK, PI3K inhibition and isoform selectivity of some new and known 2-amino-substituted-1,3-benzoxazines and substituted-1,3-naphthoxazines. Med Chem Res 2014;23:4680–91
- Morrison R, Al-Rawi JMA, Angove MJ, et al. Synthesis, structure elucidation, DNA-PK and PI3K and anti-cancer activity of 8- and 6-aryl-substituted-1-3-benzoxazines. Eur J Med Chem 2016;110:326–39
- Pritchard KM, Al-Rawi J. Reaction of Ph3P(SCN)2 with further ortho-hydroxy carboxylic acid systems, including substituted β-keto acids: synthesis of novel 2- thioxo-1,3-oxazines and their subsequent transformation with amines. Synth Commun 2008;38:4076–96
- Sethna SM, Shah RC. Pechmann condensation of methyl β-resorcylate with some β-ketonic esters. J Indian Chem Soc 1940;17:37–40
- Desai RD, Gaitonde MM, Hasan SM, Shah RC. Heterocyclic compounds. XVIII. Condensation of cyclic β-ketonic esters with methyl β-resorcylate and resacetophenone in the presence of anhydrous aluminum chloride. Proc – Indian Acad Sci Sect A 1947;25A:345–50
- Dalvi VJ, Sethna S. Bromination of coumarins. I. Bromination of 7-hydroxy-4-methylcoumarin, methyl 7-hydroxy-4-methyl-coumarin-6-carboxylate, 7-hydroxy-4-methylcoumarin-6-carboxylic acid, and their methyl ethers. J Indian Chem Soc 1949;26:359–65
- Rodriguez-Dominguez JC, Kirsch G. Zirconyl chloride: a useful catalyst in the Pechmann coumarin synthesis. Synthesis 2006;2006:1895–7
- Heppell J, Al-Rawi J. Functionalization of quinazolin-4-ones. Part 1: synthesis of novel 7-substituted-2-thioxo quinazolin-4-ones from 4-substituted-2-aminobenzoic acids and PPh3 (SCN)2. J Heterocycl Chem 2014;51:162–74
- Pritchard K, Al-Rawi J, Hughes A. Generalized method for the production of 1,3-benzoxazine, 1,3-benzothiazine, and quinazoline derivatives from 2-(hydroxy, thio, or amino) aromatic acids using triphenylphosphine thiocyanogen. Synth Commun 2005;35:1601–11
- Shah RC, Sethna SM, Banerjee BC, Chakravarti D. Pechmann's condensation of methyl β-resorcylate and β-resorcylic acid with ethyl acetoacetate. J Indian Chem Soc 1937;14:717–20
- Hedayatullah M, Huynh AH. Heterocyclic compounds from cyano esters. II. Cyanates and oxazinones of the coumarin series. Tetrahedron Lett 1976;31:1289–92