Phenanthrene derivative

For the synthesis of phenanthrene derivatives whieh may be regarded as an approaeh to eolehieine as formulated by Windaus, see Windaus and Eiehel, Sharp, and Grewe. ... 

Cevanthrol, C jH gO, crystallises from benzene in plates, m.p. 197-8°, behaves as a phenol and gives an acetyl derivative, m.p. 138-9°. X-ray analysis (Bloxmt and Crowfoot indicates that it is a phenanthrene derivative, with a hydroxyl group, possibly at C . 

Figure 3.49 The rranj-cotriplexes of a phenanthrene-derived diphosphine ligand (M = Pd, Pi).

Rigid diphosphines have been used to enforce n-ans-geometries thus with the phenanthrene-derived diphosphine (Figure 3.49, R = Et) the complexes PdLCb and PtLCl2 have closely similar geometries (Pd-P 2.307 A, Pd-Cl 2.306 A, P-Pd-P 177.4° Pt-P 2.293 A, Pt-Cl 2.304 A, P-Pt-P 177.1°)... 

General procedure for the reaction of an o-substituted aryl iodide with a diarylacetylene. Synthesis of phenanthrene derivatives. 

These are benzo[cjphenanthrene and benz[ajanthracene which, as Hewett (36) noted in 1940, are both phenanthrene derivatives. In contrast, linear structures such as naphthacene are not associated... 

As can be seen from Table 2, certain phenanthrene derivatives produce more chemiluminescence than luminol. The diphenyl derivative 33 diluminyl evidently has its benzene rings in a non-coplanar position this is apparent from the fact that this compound does not behave as a benzidine derivative under the oxidative conditions of chemiluminescence reactions. The chemiluminescence quantum yield is only about one third that of luminol 100>. 

The partially hydrogenated phenanthrene derivative 18 (entry 4) is a very moderate diene due to the steric crowding caused by the substituents and the anulated rings, and it reacts even with highly reactive dienophiles such as maleic anhydride (MA) or N-phenylmaleic imide only at high pressure. The minor product 20 in the reaction with MA obviously stems from diene 21. This can be explained by a double-bond isomerization 18 - 21 prior to the cycloaddition, certainly catalyzed by traces of acid present in the MA. In the absence of acid only the Diels-Alder adduct 22 derived from diene 18 was observed. In the reaction of diene 23 with MA (entry 5) a similar sequence of steps was observed. A [1,5] shift of the C—O bond in 23, again certainly acid-catalyzed, produces the diene 26 followed by the Diels-Alder reaction with MA to give 24 and 25. 

Takasu et al. found that at high temperature a free radical reaction of polyolefinic vinyl iodides leads to phenanthrene derivatives via a 6-endo-6-exo-polycyclization while at low temperature a mono-cyclized product is obtained through a 5-exo mode.1501... 

Reduction of phenyldiazonium chloride in acetonitrile containing a high concentration of an aromatic substrate, which can act as a free-radical trap, leads to phenylation of the substrate in 14 - 33% yields together with 50 - 50% of benzene formed by phenyl radical attack on the acetonitrile [132], Intramolecular capture of the phenyl radical, in an electrochemical equivalent of the Pschorr reaction, is much more successful and phenanthrene derivatives can be prepared in 90 - 96% yield [133],... 

The major phytotoxic principles (Fig. 3) from M. densa, were shown to be the phenanthrene derivatives erianthridin (17 9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene) and gymnopusin (18 2,7-dihydroxy-3,4,9 -trimethoxyphenan threne). ... 

Estrada S, Toscano RA, Mata R, New Phenanthrene Derivatives YtomMaxillaria densa, J Nat Prod 62 1175-1178, 1999. 

Fig. 14 Structures of cyclopenta[(2]phenanthrene derivatives and their carbocations and carboxonium ions.

The biosynthesis of aristolochic acids is considered to begin with 1-ben-zyltetrahydroisoquinoline precursors and to proceed via aporphine intermediates (5). In radioactive labeling studies, Spenser and Tiwari infused d/-tyrosine-2- C into the stem of A. sipho. The C-labeled aristolochic acid I formed lost more than 60% of its radioactivity when it was decarboxylated to the corresponding nitro phenanthrene derivative. Administration of d/-dihydroxyphenylalanine-2- C re-... 

The structural determination of aristolochic acid I (1) was first accomplished by Pailer et al. Aristolochic acid I(Ci7Hn07N) is easily soluble in alkali as well as sodium bicarbonate. It was esterified with diazomethane in dioxane to give a methyl ester (C,gHi307N), and the methyl ester was readily saponified to recover aristolochic acid I. Zinc distillation of 1 gave a phenanthrene (Scheme 6). Aristolochic acid I was decarboxylated with copper powder in quinoline to yield a nitro phenanthrene derivative (OjgHjjOjN.Sl). 

Several inhibitors of AChE have been developed for use in treating Alzheimer s disease, which requires that the drugs readily enter the CNS. These inhibitors are structurally unrelated and vary in their mechanism of inhibition, although all are reversible inhibitors. Tacrine (Cognex) is a monoamine acridine. Donepezil (Aricept) is a piperidine derivative that is a relatively specific inhibitor of AChE in the brain, with little effect on pseudo-ChE in the periphery. Galanthamine (Reminyl) is a tertiary alkaloid and phenanthrene derivative extracted from daffodil bulbs that is a reversible competitive inhibitor of AChE it also acts on nicotinic receptors. 

Chemical Class-. Natural opium alkaloid phenanthrene derivative... 

I Brand Name(s) Dilaudid, Dilaudid-5, Dilaudid HP, Hydromorph, Hydrostat IR Chemical Class Opiate derivative phenanthrene derivative... 

Brand Name(s) Astramorph PF, Avinza, DepoDur, Duramorph PF, Infumorph, Kadian, M-Eslon, MS Contin, MSIR, MS/S, Oramorph SR, Rapi-Ject, RMS, Roxanol, Roxanol-T Chemical Class Natural opium alkaloid phenanthrene derivative... 

Chemical Class Opiate derivative phenanthrene derivative I Clinical Pharmacology ... 

Dienolate alkylations have been applied successfully in syntheses of steroids and terpenoids. A highly diastereoselective application81 is the preparation of the phenanthrene derivative 35. 

The opium is obtained from the opium poppy Papaver somniferum. It contains two type of alkaloids e.g. phenanthrene derivatives (morphine, codeine thebaine) and benzyl isoquinoline derivatives (papaverine and noscapine). 

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