Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings

Mirzaei, Yousef; Weaver, Matthew; Steiger, Scott A.; Kearns, Alison K.; Gajewski, Mariusz P.; Rider, Kevin C.; Beall, Howard D.; Natale, Nicholas R.

doi:10.1016/j.tet.2012.09.084

Cited by 15 publications

(12 citation statements)

References 28 publications

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“…1 H NMR(400 MHz, CDCl 3 ) δ 8.59 (s, 1H), 8.06 (d, J=7.91 Hz, 2H), 7.66 (d, J=8.16 Hz, 2H), 7.41-7.50 (m, 4H), 3.70 (q, J=7.15, 14.31 Hz, 2H), 2.93 (s, 3H), 0.33 (t, J=7.15 Hz, 3H). Spectral data are in accord with those reported previously (Mirzaei et al, 2012).…”

Section: S21 Synthesis and Crystallizationsupporting

confidence: 90%

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Ethyl 3-(10-bromoanthracen-9-yl)-5-methyl-1,2-oxazole-4-carboxylate

Li¹,

Campbell²,

Weaver³

et al. 2013

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.025; wR factor = 0.074; data-to-parameter ratio = 18.1.In the title compound, C 21 H 16 BrNO 3 , the mean planes of the anthracene tricycle and isoxazole ring are inclined to each other at a dihedral angle of 72.12 (7) . The carboxy group is slightly out of the isoxazole mean plane, with a maximum deviation of 0.070 (5) Å for the carbonyl O atom. In the crystal, pairs of weak C-HÁ Á ÁO hydrogen bonds link the molecules into dimers, and weak C-HÁ Á ÁN interactions further link these dimers into corrugated layers parallel to the bc plane. Related literature

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Section: S21 Synthesis and Crystallizationsupporting

confidence: 90%

“…For the synthesis of anthryl isoxazoles, see: Mosher & Natale (1995); Zhou et al (1997); Han & Natale (2001); Rider et al (2010); Mirzaei et al (2012). For related structures, see: Mosher et al (1996); Han et al (2002Han et al ( , 2003; Li et al (2006Li et al ( , 2008.…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 3-(10-bromoanthracen-9-yl)-5-methyl-1,2-oxazole-4-carboxylate

Li¹,

Campbell²,

Weaver³

et al. 2013

Acta Cryst E

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“…For the synthesis of anthryl isoxazoles, see: Mosher & Natale (1995); Zhou et al (1997); Han & Natale, (2001); Rider et al (2010); Mirzaei et al (2012). For previous studies on anthryl isoxazole crystallography, see: Mosher et al (1996); Han et al (2002Han et al ( , 2003; Li et al (2006Li et al ( , 2008.…”

Section: Related Literaturementioning

confidence: 99%

“…Spectral data are in accord with those reported previously. (Mirzaei, et al, 2012) The carboxylate (0.300 g, 0.905 mmol) was taken up in 10 mL DMF to which was added a solution over 10 minutes of N-Chlorosuccinimide (NCS) (1.2 eq, 0.1461 g, 1.094 mmol) dissolved in 5 mL DMF. The solution was brought to 43°C…”

Section: S2 Experimentalmentioning

confidence: 99%

Ethyl 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate

Duncan¹,

Beall²,

Kearns³

et al. 2014

Acta Cryst E

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The asymmetric unit of the title compound, C21H16ClNO4, contains two independent molecules (A and B), each adopting a conformation wherein the isoxazole ring is roughly orthogonal to the anthrone ring. The dihedral angle between the mean plane of the isoxazole (all atoms) and the mean plane of the anthrone (all atoms) is 88.48 (3)° in one molecule and 89.92 (4)° in the other. The ester is almost coplanar with the isoxazole ring, with mean-plane dihedral angles of 2.48 (15) and 8.62 (5)°. In both molecules, the distance between the ester carbonyl O atom and the anthrone ketone C atom is about 3.3 Å. The anthrone ring is virtually planar (r.m.s. deviations of 0.070 and 0.065 Å) and adopts a shallow boat conformation in each molecule, as evidenced by the sum of the six intra-B-ring torsion angles [41.43 (15) and 34.38 (15)° for molecules A and B, respectively]. The closest separation between the benzene moieties of anthrones A and B is 5.1162 (7) Å, with an angle of 57.98 (5)°, consistent with an edge-to-face π-stacking interaction. In the crystal, weak C—H⋯O and C—H⋯N interactions link the molecules, forming a three-dimensional network.

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“…Techniques using fluorescent compounds in the visualization of tumors during surgery, referred to as tumor paint, are actively being developed. 2–4 We have recently reported on the synthesis, bioactivity and structure-activity relationship (SAR) of fluorescent anthracenyl isoxazole amides (AIMs, 1 ), 5 as well as their dimeric analogues ( 2 ) 6 depicted in Chart 1. The AIMs have shown promising activity in the National Cancer Institute’s 60-cell line screening protocol (NCI 60) and could be exploited for tumor imaging.…”

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confidence: 99%

AIMing towards improved antitumor efficacy

Weaver¹,

Kearns²,

Stump³

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Using the structure-activity relationship emerging from previous reports, and guided by pharmacokinetic properties, new AIMs have been prepared with both improved efficacy against human glioblastoma cells and cell permeability as determined by fluorescent confocal microscopy. We present our first unambiguous evidence for telomeric G4-forming oligonucleotide anisotropy by NMR resulting from direct interaction with AIMs, which is consistent with both our G4 melting studies by CD, and our working hypothesis. Finally, we show that AIMs induce apoptosis in SNB-19 cells.

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Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings

Cited by 15 publications

References 28 publications

Ethyl 3-(10-bromoanthracen-9-yl)-5-methyl-1,2-oxazole-4-carboxylate

Ethyl 3-(10-bromoanthracen-9-yl)-5-methyl-1,2-oxazole-4-carboxylate

Ethyl 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate

AIMing towards improved antitumor efficacy

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