Identification of new structural 1-benzoyl isoquinolines obtained by oxidation of papaverine.

Postaire, E.; Viel, Claude; Martinez, Didier; Likforman, J.; Hamon, Michel

doi:10.1248/cpb.35.4064

Cited by 3 publications

(13 citation statements)

References 2 publications

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“…An intense absorption band at 3300 cm -1 in the FT-IR spectrum indicated the presence of hydroxyl groups in 1. Also, absorption at 1640 cm -1 in conjunction with a 13 C NMR signal at δ 192.5 were in agreement with the presence of a conjugated ketone carbonyl group.…”

Section: Resultssupporting

confidence: 67%

“…A benzene ring bearing 1,3,4-tri-substituents was identified by 1 H NMR analysis: H-13 (δ 7.37, doublet, J meta ) 2.0 Hz), H-16 (δ 6.84, doublet, J ortho ) 8.3 Hz), and H-17 (δ 7.18, doublet of doublet, J ortho ) 8.3 Hz, J meta ) 2.0 Hz). All carbons attached to a proton were assigned on the basis of a 1 H-detected heteronuclear one bond 1 H- 13 C correlation experiment (HMQC). Thus, C-13 (δ 117.6), C-16 (δ 116.4), and C-17 (δ 126.4) for the 1,3,4tri-substitued phenyl group were identified from the 13 C NMR spectrum.…”

Section: Resultsmentioning

confidence: 99%

“…All carbons attached to a proton were assigned on the basis of a 1 H-detected heteronuclear one bond 1 H- 13 C correlation experiment (HMQC). Thus, C-13 (δ 117.6), C-16 (δ 116.4), and C-17 (δ 126.4) for the 1,3,4tri-substitued phenyl group were identified from the 13 C NMR spectrum. The remaining protons in 1 H NMR spectrum, three singlets at δ 6.95 (H-4), 7.02 (H-5), and 6.96 (H-8) were correlated to carbons at δ 103.6 (C-4), 107.5 (C-5), and 107.6 (C-8) on the basis of the HMQC experiment.…”

Section: Resultsmentioning

confidence: 99%

“…Because most carbons in compound 1 were not bonded to a proton, further information regarding the skeletal framework was sought from multiple bond protoncarbon couplings, which were identified by a 1 H-detected heteronuclear multiple bond 1 H- 13 C correlation experiment (HMBC) (Table 1). The presence of a 1,3,4- ) indicated a hydroxy substituent was attached to each of these two carbons.…”

Section: Resultsmentioning

confidence: 99%

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Discovery of a Series of Nonpeptide Small Molecules That Inhibit the Binding of Insulin-like Growth Factor (IGF) to IGF-Binding Proteins

et al. 2001

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Insulin-like growth factors (IGF-I and II) play an important role in metabolic and mitogenic activities through stimulation of the IGF-I receptor on the cell surface. Although the concentration of IGF in blood and cerebrospinal fluid is quite high (>100 nM), this large pool of IGF is biologically inactive because of its association with six distinct binding proteins, which form high-affinity complexes with IGF. Thus, inhibitors of IGF-binding proteins (IGFBPs), especially IGFBP-3, could potentially alter the distribution between the "free" and "bound" forms of IGF and thereby elevate biologically active IGF-I to exert a beneficial effect on those patients with diseases that respond to the application of exogenous IGF-I. Whereas IGF-I peptide variants, which bind to IGFBPs but not the IGF-I receptor, have been shown to be potent IGF/IGFBP inhibitors, small molecule nonpeptide IGF/IGFBP inhibitors have the potential advantages of oral bioavailability and flexible dosing regimen. Here we report the discovery of several isoquinoline analogues, exemplified by 1 and 2, which bind IGFBP-3 as well as other IGFBPs at low nanomolar concentrations. More importantly, both compounds were shown to be able to release biologically active IGF-I from the IGF-I/IGFBP-3 complex. These results point to the feasibility of developing orally active therapeutics to treat IGF-responsive diseases by optimization of the lead molecules 1 and 2.

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Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Discovery of a Series of Nonpeptide Small Molecules That Inhibit the Binding of Insulin-like Growth Factor (IGF) to IGF-Binding Proteins

et al. 2001

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“…O-methylthalicberine and thalmelatidine Thalictrum minus6 ' northalibroline* (33) and thalmelatidine Thalictrum squarrosum6' thalidasine Tiliacora triandra63. 64 noryanganine* (30), norisoyanganine* (3 1 ), nortiliacorine A, tiliacorinine 2'-N-oxide, tiliageine, and tilitriandrine* (32)…”

Section: Thalictrum Lankesterp9 Hernandezine Thalictrum Minus Hypoleu...mentioning

confidence: 99%

β-Phenylethylamines and the isoquinoline alkaloids

Bentley

1990

Nat. Prod. Rep.

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Berberis bo (23) 'viana' aromoline, berbamine, berbamunine, homoaromoline, isotetrandrine, obaberine, obamegine, oxyacanthine, patagonine, and thalrugosine aromoline, berbamine, isotetrandrine, and oxyacanthine aromoline, belarine, berbilaurine* ( 16), homoaromoline, lauberine, 7-O-demethyli~othalicberine~ and thalrugosine Berberis paucidentata" berbamine, isotetrandrine, obaberine, and oxyacanthine Berberis p01ymorpha~~ thalrugosine Cyclea r a ~e r n o s a ~~ cycleaneonine* (1 7 ) Guatteria guianensi~~~. 55 apateline, 1,2-dehydroapateline, aromoline, coclobine, daphnandrine, daphnoline, guattamine* (1 8), guattaminone* (19), 2'-norfuniferine* (20; R = Me), 2'-norguattaguianine (21 ; R = Me), 2,2'-bisnorguattaguianine (21 ; R = H), 12-O-dernethylcoclobine* (22), telobine, 1,2-dehydrotelobine, tiliageine, and 2'-nortiliageine* (20; R = H) auroamine* (23; R = Me), and marournine* (23; R = H) berbamine and isotetrandrine phaeanthine 2'-a-N-oxide* (24), and pycnanthine* (25) Berberis bumeliaefolia" Berberis laurina" Gyrocarpus arneri~anus~~ Isopyrum thalictroidesg Pycnarrhena manillensis5' 8 Azaberberines Cyclization of the dihydroisoquinolinium salt (60; R' = Me, R2 = Bz) has yielded the enamine (61), reduction of which furnished ( +_ )-alamaridine (62) and its epimer.13' This synthesis is identical with one previously r e ~0 r t e d . l ~~ Repetition of these reactions starting with (60; R' = Bz, R2 = Me) afforded an isomer of a1arna~idine.l~~ 9 Secoberberines Procumbine has been isolated from Hypecoum Ieptocarpum and from Hypecoum procumbens.

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Abnormal Retention of Some Dihydrogenophosphate-1-benzoylisoquinoline Ions Pairs Exceptionally Stable Observed in Liquid Chromatography

Postaire¹,

Todd²,

Vieil³

et al. 1988

Journal of Liquid Chromatography

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Identification of new structural 1-benzoyl isoquinolines obtained by oxidation of papaverine.

Cited by 3 publications

References 2 publications

Discovery of a Series of Nonpeptide Small Molecules That Inhibit the Binding of Insulin-like Growth Factor (IGF) to IGF-Binding Proteins

Discovery of a Series of Nonpeptide Small Molecules That Inhibit the Binding of Insulin-like Growth Factor (IGF) to IGF-Binding Proteins

β-Phenylethylamines and the isoquinoline alkaloids

Abnormal Retention of Some Dihydrogenophosphate-1-benzoylisoquinoline Ions Pairs Exceptionally Stable Observed in Liquid Chromatography

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