Phenyl-pyrrole analogues

Fig. (34). Synthesis of phenyl-pyrrole analogues of rhazinilam by Thai [92]...

In connection with the elucidation of the structures of the products obtained upon reaction of the tropone (496) with perchloric acid, the 6-methoxy-substituted derivatives have been prepared by reaction of (496) with methyl iodide and silver fluoroborate. -Comparison of u.v. spectra indicated that the salts between the tropones (496) and perchloric acid were 6-hydroxy-derivatives of the perchlorate of (497). U.v. and n.m.r. spectra of the systems (496)—(499) are discussed and their properties and reactivities compared with the corresponding JV-phenyl-pyrrole analogue. A preliminary report of the polarographic, i.r., and u.v. spectroscopic properties, as well as the dipole moments, of both the C-annelated systems (496) and (497) without methyl groups in the thiophen ring and also the ion (500) with alkyl, hydroxy, and methoxy-groups in the seven-membered ring has been published. Values of piirR+ between 6 and 7 have been obtained for this system. The spectroscopic properties of metallocene derivatives such as (501)—(503) have also... 

Other phenyl-pyrrole and phenyl-pyridine analogues of rhazinilam, having seven to nine-membered B-rings, have been synthesized using a Suzuki-Miyaura biaryl coupling to install the biaryl bond, Fig. (37). 

New phenyl pyrroles are produced55 vhen certain analogues of tryptophan (dl-6-fluorotryptophan and dl-7-methyltrypto-phan) are added to pyrrolnitrin-producing cultures. The new compounds, it -fluoropyrrolnitrin and 3 > thyl-3 -dechloro-pyrrolnitrin, still possessed significant antifungal activity. The x-ray crystal structures of pyrrolnitrin and -fluoro-pyrrolnitrin have been determined.5° 57... 

The primary fragmentations of 5-methylsulfonyl-6-phenyl-2-pyridone (41) and its 3,4-dihydro analogue (42) are dominated by the methylsulfonyl substituent and not by the pyridone moiety26. Equation (18) summarizes the most important primary fragmentations and shows that the pyridone ions m/z 186 and 170 yield the pyrrole-type ions m/z 158 and 142 only after the sulfonyl side-chain has been broken off. Since the mass spectrum... 

M = Eu(III), Y(III), Lu(III)] 8-16%. These protonated compounds were isolated as the sole product, in contrast to the similar reactions with TBPPH2, where the non-protonated analogues Lnnl(Pc)(TBPP) (TBPP, 5,10,15,20-tetrakis[(4- ert-butyl)phenyl]-porphyrin) were obtained instead [106]. These results clearly show that the inversion of a pyrrole ring in N-confused porphyrins can stabilize the protonated complexes. 

In the case of atorvastatin, a lH-pyrrole ring system was selected [3], The synthetic 2-(4-fluoro-phenyl)-5-isopropyl derivative (Fig. 4.5) inhibited [uC]-acetate conversion to cholesterol in a crude rat liver homogenate. A optimization of its 3,4-disubstituted analogues resulted in atorvastatin. 

With the lithium amide of the diamine (,S )-l-isopropylamino-1-phenyl-2-pyrrol idinyl-ethane (12), an analogue of the ether amide shown previously, almost no mixed complexes were formed with n-BuLi (Li-12/n-BuLi), i.e. the equilibrium was almost completely shifted toward the homoaggregates. The apparent equilibrium constant, K, of Scheme 5 was determined to be 0.14 M. 

Non-aromaticity of As-analogues of pyrroles has been proved beyond all doubt by various chemical and spectroscopic methods as well as by quantum chemical calculations . Two such compounds have been studied by UPS 1-phenyl-2,5-dimethylarsole and 2-t-butyl-3-methyl-l,3-benzazarsole, and both spectra have been interpreted accordingly. The low-IE region of the spectrum of the former compound features three bands at... 

In the series of N-4 unsubstituted arylpiperazines 7-methoxy-l-naphthylpiperazine is the most potent S-HTja ligand (Kj=1.8 nM). The 2-methoxy analogue is more than 2 decades less active. This result indicates that the N-1 phenyl ring of 1-naphthylpiperazine mimics the pyrrole ring of 5-HT. The benz-fused phenyl ring of 1-naphthylpiperazine corresponds to the phenyl ring of 5-HT... 

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