ChemInform Abstract: ORGANOPHOSPHORUS COMPOUNDS. 108. SYNTHESIS OF FLUORESCENT AND CHEMOSELECTIVE REAGENTS FOR SPECIFIC DETECTION AND PROTECTION OF BIOLOGICALLY IMPORTANT FUNCTIONAL GROUPS

Horner, L.; Flemming, Hans‐Wolfram

doi:10.1002/chin.198544229

Cited by 1 publication

(3 citation statements)

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“…1.4-Dihydroxy-6-[3'-(methylcarboxy)-4'-hydroxyphenyl]naphthalene (20). Following a procedure analogous to that utilized for the preparation of 12, compound 20 was obtained as a dark purple solid (123 mg, 94%) which was contaminated with a small amount of 9: NMR (DMSO-dg) 10.53 (s, 1H, 2'-OH), 9.42 (s, 1H, OH), 9.38 (s, 1H, OH), 8.21 (d, 1H, J = 1.7 Hz, Hg), 8.13 (d, 1H, J = 2.3 Hz, Hg-), 8.10 (d, 1H, J = 8.8 Hz, Hg), 7.94 (dd, 1H, J = 8.6, 2.3 Hz, H*), 7.70 (dd, 1H, J = 8.8,1.7 Hz, H7), 7.12 (d, 1H, J = 8.6 Hz, Hg ), 6.66 (q, 2H, J = 8.1 Hz, H2 and Hg), 3.92 (s, 3H, OCHg).…”

Section: Methodsmentioning

confidence: 99%

“…1.2-Dihydroxy-6-(S'-salicy 1 )naphthalene (11). Treatment of 23 with pyridine-HCl for 1 h as described for compound 9 afforded 11 as a dark green solid (83%): mp > 200 °C dec; NMR (DMSO-de) 11.3 (br s, 1H, C02H), 9.33 (s, 1H, OH), 8.88 (s, 1H, OH), 8.12 (d, 1H, J = 2.0 Hz, Hy), 8.05 (d, 1H, J = 8.8 Hz, Hg), 7.95 (br s, 1H, H5), 7.93 (dd, 1H, J = 8.7, 2.0 Hz, Hy), 7.63 (d, 1H, J = 8.8 Hz, H7), 7.35 (d, 1H, J = 8.7 Hz, H3), 7.14 (d, 1H, J = 8.7 Hz, 4 7.07 (d, 1H, J = 8.7 Hz, Hy); FABMS m/z 295 (M-H)-. Anal.…”

Section: Methodsmentioning

confidence: 99%

“…2,3-Dihydroxy-6-(5'-salicyl)naphthalene (10). Treatment of 28 with pyridine-HCl (1 h) as described for compound 9 afforded 10 as a brown powder (63 %): mp 231-233 °C; NMR (DMSOde) 11.3 (br s, 1H, C02H), 9.59 (s, 1H, OH), 9.56 (s, 1H, OH), 8.09 (d, 1H, J = 2.3 Hz, Hy), 7.88 (dd, 1H, J = 8.6, 2.3 Hz, Hi-), 7.80 (s, 1H, H6), 7.63 (d, 1H, J = 8.5 Hz, H8), 7.44 (dd, 1H, J = 8.5,1.7 Hz, H7), 7.18 (s, 1H), 7.10 (s, 1H), 7.05…”

Section: Methyl 2-methoxy-5-(trimethylstannyl)benzoate (27)mentioning

confidence: 99%

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Hydroxylated 2-(5'-salicyl)naphthalenes as protein-tyrosine kinase inhibitors

Smyth¹,

Stefanová²,

Horak³

et al. 1993

J. Med. Chem.

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The salicyl group figures prominently in several potent protein-tyrosine kinase (PTK) inhibitors, including the fermentation product lavendustin A (3), the salicylsulfonyl nitrostyryl 30, and our recently reported salicyl-containing stilbene 7. Taking compound 7 and the isomeric 8 as lead structures, bicyclic nuclei 9-12 were prepared as conformationally constrained mimetics in which the hydroxyphenyl rings of 7 and 8 are held coplanar with the stilbene ethylene bridge. A similar approach with styryl-based PTK inhibitors of structure 1 previously yielded analogues 2 with enhanced potency. In the present case, however, the resulting salicyl-containing bicyclics exhibited extremely poor inhibitory potency when examined against autophosphorylation of immunoprecipitated p56lck PTK preparations. The implications of these results are discussed as they relate to the potential ways in which salicyl-containing stilbenes may be oriented relative to styryl-based inhibitors of type 1 and to an emerging class of potent aryl-substituted bicyclic inhibitors exemplified by compound 31.

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Section: Methodsmentioning

confidence: 99%