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Production of 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters

4-Alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters are intermediate products for the production of cerebrally-active pharmaceutical products. The advantageous process for production of the new intermediate products is described.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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As acaricides and insecticides aryl sulfide derivatives and aryl sulfur oxide derivatives (by machine translation)

This invention relates to aryl sulfide derivatives and aryl sulfur oxide derivatives, its as acaricides and insecticides for controlling animal pests and the use of the method for its preparation and intermediate products. Aryl sulfide derivatives and aryl sulfur oxide derivatives having a general structure (I) Wherein each group is No.2. the meaning stated in the specification. (by machine translation)

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Pyrroline – Wikipedia,
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Synthesis and protein kinase C inhibitory activities of acyclic balanol analogs that are highly selective for protein kinase C over protein kinase A

A series of balanol analogs in which the perhydroazepine ring and the p- hydroxybenzamide moiety were combined into an acyclic linked unit have been prepared and evaluated for their inhibitory properties against the serine/threonine kinase PKC. Several low-micromolar to lownanomolar inhibitors of the alpha, beta'(I), beta(II), gamma, delta, epsilon, and eta PKC isozymes were prepared. In general, these acyclic balanol analogs were found to be highly selective for PKC over the serine/threonine kinase PKA. The type and number of atoms linking the benzophenone ester to the p-hydroxyphenyl group necessary for optimal PKC inhibition were investigated. The most potent compounds contained a three-carbon linker in which the carboxamide moiety of balanol had been replaced by a methylene group. The effect of placing substituents on the three-carbon chain was also investigated. The preferred compounds contained either a 2-benzene-sulfonamido (6b) or a 1-methyl (21b) substituent. The preferred compounds 6b and 21b were tested against a panel of serine/threonine kinases and found to be highly selective for PKC. The more active enantiomer of 6b, (S)-12b, was 3-10-fold more active than the R- enantiomer against the PKC isozymes. The effect of making the analogs more rigid by making the three-carbon chain part of a five-membered ring, but with retention of the methylene replacement for the carboxamide moiety, led to potent PKC inhibitors including anti-substituted pyrrolidine analog 35b and the most potent PKC inhibitor in the series, anti-substituted cyclopentane analog 29b. The anti cyclopentane analog 29b was a low-micromolar inhibitor of the PMA-induced superoxide burst in neutrophils, and its carboxylic ester was a high-nanomolar inhibitor of neutrophils. Finally esterification of 21b, (S)-12b, and 35b turned these potent PKC inhibitors into low-micromolar inhibitors of neutrophils.

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Pyrroline – Wikipedia,
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Scaffold Diversity from N-Acyliminium Ions

N-Acyliminium ions are powerful reactive species for the formation of carbon-carbon and carbon-heteroatom bonds. Strategies relying on intramolecular reactions of N-acyliminium intermediates, also referred to as N-acyliminium ion cyclization reactions, have been employed for the construction of structurally diverse scaffolds, ranging from simple bicyclic skeletons to complex polycyclic systems and natural-product-like compounds. This review aims to provide an overview of cyclization reactions of N-acyliminium ions derived from various precursors for the assembly of structurally diverse scaffolds, covering the literature over the past 12 years (from 2004 to 2015).

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Dihydropyrrolopyrazol-6-one MCHR1 antagonists for the treatment of obesity: Insights on in vivo efficacy from a novel FLIPR assay setup

Our investigation of the structure-activity and structure-liability relationships for dihydropyrrolopyrazol-6-one MCHR1 antagonists revealed that off-rate characteristics, inferred from potencies in a FLIPR assay following a 2 h incubation, can impact in vivo efficacy. The in vitro and exposure profiles of dihydropyrrolopyrazol-6-ones 1b and 1e were comparable to that of the thienopyrimidinone counterparts 41 and 43 except for a much faster MCHR1 apparent off-rate. The greatly diminished dihydropyrrolopyrazol-6-one anti-obesity response may be the consequence of this rapid off-rate.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1

A merged conjugate addition/oxidative coupling sequence that represents an efficient strategy for preparing structurally diverse pyrroles has been developed. Success of the method hinged upon the controlled oxidative coupling of unsymmetrical silyl bis-enol ether intermediates, formed by the 1,4-addition of a Grignard reagent with subsequent enolate trapping by a (chloro)silylenol ether. The process was applied to the first enantioselective syntheses of the biologically active pyrrolophane natural products, metacycloprodigiosin and prodigiosin R1.

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Pyrroline – Wikipedia,
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Synthesis and anti-cancer activity of C-ring-functionalized prodigiosin analogues

Prodigiosin is the parent member of the 4-methoxypyrrolyldipyrromethene family of natural products and is known for its anti-cancer activity. A new series of analogues was synthesized, incorporating pendent functional esters and beta-carbonyl substituents on the C-ring. The beta-carbonyl group allowed for the facile isolation of the prodigiosenes, and the pendent esters allow for further derivatization. The novel prodigiosenes generally retain the anti-cancer activity of prodigiosin in 60 human cell lines derived from nine cancer cell types, with neither the conjugated /3-carbonyl group, as either ketone or ester, nor the pendent ester significantly reducing the anti-cancer activity of the core skeleton.

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Pyrroline – Wikipedia,
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Synthesis of the tricyclic core of the marine alkaloid lepadiformine

A stereoselective synthesis of the tricyclic core in racemic form of the marine alkaloid Lepadiformine is described from 4-methoxy-3-pyrrolin-2-one (methyl tetramate). Key steps involve 5,5-dialkylation of the tetramate, metathesis closure to an A/C 1-azaspirocycle and stereoselective hydrogenation for the trans A/B 1-azadecalin system.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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BODIPY-based ratiometric fluoroionophores with bidirectional spectral shifts for the selective recognition of heavy metal ions

Two novel asymmetric BODIPY fluoroionophores with dipicolylamine (BDP-DPA, dipicolylamine: bis(pyridylmethyl)) and terpyridine (BDP-TPY) are described. These fluoroionophores display opposite wavelength responses on complexation with heavy metal ions. Furthermore, the fluorescence spectra vary depending on the ionic species. In particular, BDP-DPA shows a high affinity toward Cr3+ and upon complexation, the fluorescence spectrum blue-shifts from 591 to 566 nm. In contrast, BDP-TPY preferentially binds to Zn2+ and the fluorescence spectra red-shifts from 539 to 567 nm. BDP-TPY is the first example of asymmetric BODIPY with a pyridyl receptor at the 3 position showing redshifted fluorescence by complexation with metal ions. The concentration of each metal ion was successfully determined by ratiometric measurement. The wavelength-responses characteristics of these fluoroionophores could be very useful in the development of novel ratiometric fluoroionophores for metal ions.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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SYNTHESIS OF 5-SUBSTITUTED 4-O-METHYL TETRAMATES

4-Methoxy-Delta3-pyrrolin-2-ones (4-O-methyl tetramates) are alkylated at C-5 via a lithio-derivative; an N-substituent may be introduced either during or after heterocycle formation.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem