Azaindol‐Derivate II: Synthese und analgetische Wirkung von Pyrazolo[1,5‐a]pyridinen

Gmeiner, Peter; Schünemann, Jürgen

doi:10.1002/ardp.19883210905

Cited by 12 publications

(3 citation statements)

References 7 publications

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“…5 Hz,1H,CH2I),l H ,, 3.68 (dd, J = 9.5/2.9 Hz, l H , CH21), 3.75 (s, 3H, OCH3), 3.81 5), 30.3, 32.4 (C-6), 35.5, 37.6 (C-5a), 47.7, 47.8 (C-3), 52. 2,52.3 (OCH3),56.6,120.1,140.5,145,170.9,171.4 (C02R),190.5,191.1 (CO) 5,6, pyrazolo ( Methyl (f)-3,4,5,Sa,6,7,8,9-0ctahydro-9-oxo-2,2a-diazabenzo-/cdjazulene-8-carboxylate (9b): A solution of 376 mg (1 mmol) of 7b in 15 ml of THF was added to 24 mg (1 mmol) of NaH. The suspension was stirred at room temp.…”

Section: Methodsmentioning

confidence: 99%

Stereoelectronically controlled cyclization reactions on the way to peri‐fused tetrahydropyrazolo[1,5‐a]pyridines as aza analogs of ergoline partial structures

Gmeiner¹,

Sommer²

1991

Liebigs Ann. Chem.

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The synthesis of the 3-substituted tetrahydropyrazolopyridin-4-ylalkyl iodides ?a, ?b, 8a and 8b as well as their behavior towards anionic cyclization conditions have been investigated. An (enol endo)-exo-tet-type ring closure only proceeds when a seven-membered ring is annulated (Sb, lob). Otherwise, treatment of the P-keto ester ?a with NaH results in 0-alkylation to yield the stereoelectronically favored (Z)-enol ether 13 a, which can be isomerized to the thermodynamically more stable (E) isomer 13b. Various attemps to achieve ring closure of the methyl ketone 8a failed; instead, p-elimination is observed. Annulation of a six-membered carbocycle is acchieved when the triester l ? is treated by a Dieckmann condensation to give the tricyclic products 18 and 19.Ergoline derivatives (1) as well as their ABC tricyclic and BC bicyclic analogs are widely studied substrates with remarkable pharmacological properties '). The main characteristic of that group of compounds is their activity towards different receptors, namely the dopamine, serotonin, and adrenergic binding sites. In search of more selective dopamine agonists and antagonists which might also differentiate between dopamine receptor subtypes, we are investigating biand tricyclic analogs which are devoid of an aromatic NH moiety. Thus, we elaborated an EPC synthesis of the highly CNS active aminoindolizidines 2a and 2b2). We also prepared the pyrazolochinolinecarboxylate derivatives 3 a and 3 b3), which can be converted into the pharmacologically relevant amines 3c and 3d in a Curtius rearrangement4).

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Section: Methodsmentioning

confidence: 99%

Stereoelectronically controlled cyclization reactions on the way to peri‐fused tetrahydropyrazolo[1,5‐a]pyridines as aza analogs of ergoline partial structures

Gmeiner¹,

Sommer²

1991

Liebigs Ann. Chem.

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“…Besides a few routine reactions, [211] some electrophilic substitutions and transformations via lithiation are of preparative importance. Besides a few routine reactions, [211] some electrophilic substitutions and transformations via lithiation are of preparative importance.…”

Section: Synthesis By Substituent Modificationmentioning

confidence: 99%

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

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In contrast to Section 12.5.1.1.1.1, where in most cases the first reaction step is the quaternization of a pyridin-2-amine derivative followed by nucleophilic attack of the 2-amino group on an appropriate functional group to form the imidazole ring, several ring closures have been elaborated starting from substituted pyridin-2-amines. In these cases, the â-carbon atom of the carbon chain attached to the 2-amino group bears an appropriate functional group, and a nucleophilic attack of the pyridine ring nitrogen atom at this center results in formation of the imidazole ring. Such syntheses are shown in Scheme 8.

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“…A represent CoMFA results, whereas B refer to CoMSIA results. Training set compounds (1-45) are indicated by open circles, test set compounds by filled circles(46)(47)(48)(49)(50)(51)(52)(53)(54) or filled rhombi(55)(56)(57).…”

mentioning

confidence: 99%

1,4-Disubstituted aromatic piperazines with high 5-HT2A/D2 selectivity: Quantitative structure-selectivity investigations, docking, synthesis and biological evaluation

Möller

Salama

Kling

et al. 2015

Bioorganic & Medicinal Chemistry

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Azaindol‐Derivate II: Synthese und analgetische Wirkung von Pyrazolo[1,5‐a]pyridinen

Cited by 12 publications

References 7 publications

Stereoelectronically controlled cyclization reactions on the way to peri‐fused tetrahydropyrazolo[1,5‐a]pyridines as aza analogs of ergoline partial structures

Stereoelectronically controlled cyclization reactions on the way to peri‐fused tetrahydropyrazolo[1,5‐a]pyridines as aza analogs of ergoline partial structures

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

1,4-Disubstituted aromatic piperazines with high 5-HT2A/D2 selectivity: Quantitative structure-selectivity investigations, docking, synthesis and biological evaluation

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