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Process for the production of 4-alkoxy-3-pyrrolin-2-ones

Process for the production of 4-alkoxy-3-pyrrolin-2-ones, which are preferred intermediate products for the production of cerebrally-active pharmaceutical products.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Influence of the A-ring on the proton affinity and anticancer properties of the prodigiosins

Prodigiosin (Prod, 1) is the parent member of a class of polypyrrole natural products that exhibit promising immunosuppressive and anticancer activities. They are known to act as H+/Cl- symporters possibly through electrostatic binding to Cl- that facilitates proton-coupled transmembrane transport of halides. This activity has been ascribed to their promotion of apoptosis by acidification of the intracellular pH (pHi). Since the protonated pyrromethene chromophore of Prod (1) is expected to play a critical role in pHi regulation, and the A-pyrrole ring is known to be important for anticancer activity, we prepared several Prod analogues with various A-ring systems to determine their proton affinity in 1:1 (v/v) acetonitrile (MeCN)/H2O and anticancer properties against HL-60 cancer cells. Our studies show that the A-ring strongly influences the proton affinity of the pyrromethene entity. Replacement of the C-2 methoxy group in 2,4-dimethoxy-pyrromethene 3 (apparent pKa = 4.95) with the A-pyrrole ring to generate the Prod analogue 5 raised the apparent pKa to 7.54 (increase by 2.59 pK units) and caused a 76 nm red shift in the UV-vis absorbance of the protonated species (AH+). The A-pyrrole NH atom plays an important role in stabilization of AH+, as its replacement with O or S atoms decreases the apparent pKa by 0.79 and 1.07 pK units, respectively. A 4-substituted phenyl series of Prod analogues 8-14 exhibited a linear correlation with the Hammett sigmap values. Within the phenyl series, two Prod analogues were found to inhibit colony formation of HL-60 cancer cells, although the inhibition did not correlate with the proton affinity of the pyrromethene entity. The implications of these findings with regard to the anticancer activities of the prodigiosins are discussed.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Indolyl-pyrrolydenemethylpyrrole derivatives and process for their preparation

The present invention relates to substituted (1H-indol-2-yl)-5[(2H-pyrrol-2-ylidene) methyl]-1H-pyrrole compounds and their use as immunomodulating agents, to the preparation of the compounds and to pharmaceutical compositions comprising them.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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PYRAZOLE DERIVATIVES AS SGC STIMULATORS

There are described imidazole and pyrazole derivatives which are useful as stimulators of sGC, particularly NO-independent, heme-dependent stimulators. These compounds are also useful for treating, preventing or managing various disorders that are herein disclosed.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Photoinduced cytotoxicity and thioadduct formation by a prodigiosin analogue

(Chemical Equation Presented) The prodigiosin alkaloid 1 and the synthetic analogue 2 show photoinduced cytotoxicity against HL-60 cancer cells. Photoirradiation of 1 and 2 causes photofading, photooxidation, and thioadduct formation. These results provide a model for the redox properties of prodigiosins that play a role in their biological activity and provide a new way to functionalize their pyrromethene entity with water-soluble thiol groups.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Enantioselective total synthesis and confirmation of the absolute and relative stereochemistry of streptorubin B

The enantioselective total synthesis of the pyrrolophane natural product streptorubin B is described. Key steps in the concise route include the application of a one-pot enantioselective aldol cyclization/Wittig reaction and an anionic oxy-Cope rearrangement to forge the crucial 10-membered ring. Comparisons between CD spectra of synthetic and natural samples of streptorubin B coupled with X-ray crystallography allowed for the determination of the absolute stereochemistry of this natural product for the first time. These studies also provided unambiguous proof of the relative configuration between the butyl side chain and the bispyrrole subunit. Additional studies revealed a novel atropstereoselective Paal-Knorr pyrrole condensation and provided fundamental experimental insight into the barrier for atropisomerization of the natural product.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Antimalarial activity of natural and synthetic prodiginines

Prodiginines are a family of linear and cyclic oligopyrrole red-pigmented compounds. Herein we describe the in vitro antimalarial activity of four natural (IC50 = 1.7-8.0 nM) and three sets of synthetic prodiginines against Plasmodium falciparum. Set 1 compounds replaced the terminal nonalkylated pyrrole ring of natural prodiginines and had diminished activity (IC 50 > 2920 nM). Set 2 and set 3 prodiginines were monosubstituted or disubstituted at either the 3 or 5 position of the right-hand terminal pyrrole, respectively. Potent in vitro activity (IC50 = 0.9-16.0 nM) was observed using alkyl or aryl substituents. Metacycloprodiginine and more potent synthetic analogues were evaluated in a P. yoelii murine patent infection using oral administration. Each analogue reduced parasitemia by more than 90% after 25 (mg/kg)/day dosing and in some cases provided a cure. The most favorable profile was 92% parasite reduction at 5 (mg/kg)/day, and 100% reduction at 25 (mg/kg)/day without any evident weight loses or clinical overt toxicity.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

In heterogeneous catalysis, the catalyst is in a different phase from the reactants. Formula: C5H7NO2, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 69778-83-2, name is 4-Methoxy-1H-pyrrol-2(5H)-one. In an article£¬Which mentioned a new discovery about 69778-83-2

TOTAL SYNTHESIS OF ANTIBIOTIC ALTHIOMYCIN

Antibiotic althiomycin was totally synthesized from D-cysteine via the procedures of the coupling with sodium salt of pyrrolinone, hydroxymethylation, and the coupling with the thiazole part, succesively.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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A concise synthesis of butylcycloheptylprodigiosin

A short and efficient total synthesis of the tripyrrole alkaloid butylcycloheptylprodigiosin is described. Key to the brevity of the approach is a two-step synthesis of macrocyclic formylpyrrole 4 from cyclononenone 6.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Synthesis of gallinamide A analogues as potent falcipain inhibitors and antimalarials

Analogues of the natural product gallinamide A were prepared to elucidate novel inhibitors of the falcipain cysteine proteases. Analogues exhibited potent inhibition of falcipain-2 (FP-2) and falcipain-3 (FP-3) and of the development of Plasmodium falciparum in vitro. Several compounds were equipotent to chloroquine as inhibitors of the 3D7 strain of P. falciparum and maintained potent activity against the chloroquine-resistant Dd2 parasite. These compounds serve as promising leads for the development of novel antimalarial agents.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem