Aldol condensation/hydrogenation for jet fuel from biomass-derived ketone platform compound in one pot

Seven novel N-alkyl-plinabulin derivatives with aryl groups moieties (nitroquinoline, 1,4-dihydroquinoline, 4-methoxybenzene, and 4-chlorobenzene) have been synthesized via aldol condensation and alkylation in one-pot, and tested for their cytotoxicity against 4 cancer cell lines (KB, HepG2, Lu, and MCF7). Compounds ( Z)−3-((6,8-dimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)piperazine-2,5-dione (5a), ( Z)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)−3-((1,6,8-trimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)piperazine-2,5-dione (5b), and ( Z)−3-(( Z)−4-chlorobenzylidene)−1,4-dimethyl-6-((8-methyl-4-nitroquinolin-2-yl)methylene)piperazine-2,5-dione (8) showed strong cytotoxicity against 3 of the cancer cells lines (KB, HepG2 and Lu) with IC50 values ranging from 3.04 to 10.62 µM. The quinoline-derived compounds had higher cytotoxic activity than the benzaldehyde derivatives. The successful synthesis of these derivatives offers useful information for the development of more potent vascular disrupting agents based on plinabulin.

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Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽

10.1055/s-0036-1591582 ◽

2018 ◽

Vol 29 (12) ◽

pp. 1589-1592 ◽

Cited By ~ 6

Author(s):

Abolfazl Olyaei ◽

Mahnaz Saraei ◽

Reyhaneh Khoeiniha

Keyword(s):

Michael Addition ◽

Aldol Condensation ◽

Ring Closure ◽

Dehydration Reaction ◽

One Pot ◽

Catalyst Free ◽

One Pot Synthesis ◽

Tandem Process ◽

First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

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One-pot reaction-separation process to produce jet fuel

Energy Conversion and Management X ◽

10.1016/j.ecmx.2021.100155 ◽

2022 ◽

Vol 13 ◽

pp. 100155

Author(s):

Shaoqu Xie ◽

Zhuoxi Li ◽

Guodian Zhu ◽

Conghua Yi

Keyword(s):

Jet Fuel ◽

Separation Process ◽

One Pot

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A new aldol condensation of .alpha.-allenic esters with aldehydes, including a one-pot synthesis of enyne compounds

The Journal of Organic Chemistry ◽

10.1021/jo00074a020 ◽

1993 ◽

Vol 58 (22) ◽

pp. 5952-5957 ◽

Cited By ~ 57

Author(s):

Sadao Tsuboi ◽

Hirofumi Kuroda ◽

Satoshi Takatsuka ◽

Takashi Fukawa ◽

Takashi Sakai ◽

...

Keyword(s):

Aldol Condensation ◽

One Pot ◽

One Pot Synthesis ◽

Allenic Esters

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ChemInform Abstract: Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application Toward the Total Synthesis of Aristoyagonine (XII).

ChemInform ◽

10.1002/chin.201406205 ◽

2014 ◽

Vol 45 (6) ◽

pp. no-no

Author(s):

Hye Sun Lim ◽

Young Lok Choi ◽

Jung-Nyoung Heo

Keyword(s):

Total Synthesis ◽

Aldol Condensation ◽

Cascade Reaction ◽

One Pot

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Chalcones and Flavanones Bearing Hydroxyl and/or Methoxyl Groups: Synthesis and Biological Assessments

Applied Sciences ◽

10.3390/app9142846 ◽

2019 ◽

Vol 9 (14) ◽

pp. 2846 ◽

Cited By ~ 3

Author(s):

Gonçalo P. Rosa ◽

Ana M. L. Seca ◽

Maria do Carmo Barreto ◽

Artur M. S. Silva ◽

Diana C. G. A. Pinto

Keyword(s):

Aldol Condensation ◽

Biological Activities ◽

Sodium Hydride ◽

Antitumor Activities ◽

One Pot ◽

Substitution Pattern ◽

Control Drug ◽

Wide Range ◽

Biological Assessments ◽

Isomeric Structures

Chalcones and flavanones are isomeric structures and also classes of natural products, belonging to the flavonoid family. Moreover, their wide range of biological activities makes them key scaffolds for the synthesis of new and more efficient drugs. In this work, the synthesis of hydroxy and/or methoxychalcones was studied using less common bases, such as sodium hydride (NaH) and lithium bis(trimethylsilyl)amide (LiHMDS), in the aldol condensation. The results show that the use of NaH was more effective for the synthesis of 2′-hydroxychalcone derivatives, while LiHMDS led to the synthesis of polyhydroxylated chalcones in a one-pot process. During this study, it was also possible to establish the conditions that favor their isomerization into flavanones, allowing at the same time the synthesis of hydroxy and/or methoxyflavanones. The chalcones and flavanones obtained were evaluated to disclose their antioxidant, anticholinesterasic, antibacterial and antitumor activities. 2′,4′,4-Trihydroxychalcone was the most active compound in terms of antioxidant, anti-butyrylcholinesterase (IC50 26.55 ± 0.55 μg/mL, similar to control drug donepezil, IC50 28.94 ± 1.76 μg/mL) and antimicrobial activity. 4′,7-Dihydroxyflavanone presented dual inhibition, that is, the ability to inhibit both cholinesterases. 4′-Hydroxy-5,7-dimethoxyflavanone and 2′-hydroxy-4-methoxychalcone were the compounds with the best antitumor activity. The substitution pattern and the biological assay results allowed the establishment of some structure/activity relationships.

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