Synthesis and psychotropic activity of pyrazidole analogs

Grinev, A. N.; Shvedov, V. I.; Krichevskii, E. S.; Romanova, O. B.; Altukhova, L. B.; Kurilo, G. N.; Андреева, Н. И.; Golovina, S. M.; Mashkovskii, M. D.

doi:10.1007/bf00758834

Cited by 5 publications

(4 citation statements)

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“…The indole ring system is present in a number of natural products, many of which are found to possess psychotropic (Grinev, Trofimkin, Lomanova, Andreeva & Mashkovskii, 1978), antidepressant (Grinev et al, 1984) and hypertensive (Merk, 1971) properties. They also exhibit antirnicrobial (EI-Sayed, Bamhart, Ammon & Wassel, 1986) and anti-inflammatory (Rodriguez, Temprano, Esteban-Calderon, Martinez-Ripoll & GarciaBlanco, 1985) activity.…”

Section: Commentmentioning

confidence: 99%

1-(Phenylsulfonyl)-2-[1-(phenylsulfonyl)-2-(3,4,5-trimethoxyphenyl)ethyl]indole

Seetharaman¹,

Rajan²

1995

Acta Crystallogr C

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The title compound contains an indole ring system with two phenylsulfonyl groups and one 3,4,5-trimethoxyphenyl group as exocyclic substituents. The methoxy groups in the 3,4,5-trimethoxyphenyl moiety are twisted with respect to the plane of the ring. One of the phenylsulfonyl ring systems and the ring of the 3,4,5-trimethoxyphenyl group are nearly perpendicular to the indole ring system, while the other phenylsulfonyl ring system is inclined at an angle of 30 ° to it.

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Section: Commentmentioning

confidence: 99%

1-(Phenylsulfonyl)-2-[1-(phenylsulfonyl)-2-(3,4,5-trimethoxyphenyl)ethyl]indole

Seetharaman¹,

Rajan²

1995

Acta Crystallogr C

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“…Although a -fused azapolycyclic indoles are less studied than the b -fused, recently some papers related to the chemistry and the pharmacology of pyrazino[1,2- a ]indole nucleus have appeared in the literature. Whereas the synthesis of 1-oxopyrazino[1,2- a ]indole derivatives was widely explored, the preparation of simple pyrazino- and 3,4-dihydropyrazino[1,2- a ]indoles 8 has been less examined. For example, Hegedus 7a prepared the pyrazinoindole nucleus in moderate yield starting from N -allylskatole by activation of the olefin moiety with a strong electrophilic palladium complex as Pd(MeCN) 4 (BF 4 ) 2 followed by treatment with acetonitrile.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Cyclization of δ-Iminoacetylenes: A New Entry to Pyrazino[1,2-a]indoles

et al. 2005

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[reaction: see text] The synthesis of the pyrazino[1,2-a]indole nucleus was achieved by intramolecular cyclization of several 2-carbonyl-1-propargylindoles in the presence of ammonia. The reaction conditions were optimized using microwave heating and a pool of catalysts. Cyclization of 1-alkynylindole-2-carbaldehydes was easily accomplished under standard heating conditions, whereas microwave heating contributed to reduced reaction times and improved overall yields. Moreover, a fine-tuning of the microwave irradiation time made possible the selective synthesis of both pyrazino[1,2-a]indole isomers. TiCl4 proved the catalytic system of choice to achieve pyrazinoindoles in satisfactory yields starting from 1-alkynyl-2-acetylindoles and 1-alkynyl-2-benzoylindole derivatives. Also in these cases, microwave heating contributed to faster reactions and improved yields. The uncatalyzed versus catalyzed reaction mechanism is discussed.

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“…Chromanone derivatives possess antiviral (Xu et al, 1998), antifungal (Emami et al, 2004;Yang et al, 2002) and anti-inflammatory (Konieczny et al, 1976) activities. The indole ring system is present in a number of natural products (Nigović et al, 2000), many of which are found to possess psychotropic (Grinev et al, 1978) and antidepressant (Grinev et al, 1984) properties. In view of its medicinal importance, the crystal structure and molecular structure determination of the title compound, (I), was carried out by X-ray diffraction.…”

Section: Commentmentioning

confidence: 99%