ChemInform Abstract: SYNTHESIS OF 1,2‐DIHYDRO‐3H‐PYRROLO(1,2‐A)PYRROLE‐1‐CARBOXYLIC ACIDS AND HOMOLOGOUS PYRIDINE AND AZEPINE ANALOGS THEREOF

Carpio, Humberto; Galeazzi, E.; Greenhouse, Robert; Guzmán, A.; Velarde, E.; Antonio, Y.; Franco, Fidencio; Leon, A.; Pérez, Virginia; Salas, Raquel; Valdes, D.; Ackrell, J.; Cho, D.; Gallegra, P.; Halpern, O.; Koehler, R. E.; Maddox, Michael L.; Muchowski, Joseph M.; Prince, Anthony; Tegg, Derek; Thurber, T. Craig; Horn, A. R. Van; Wren, D. L.

doi:10.1002/chin.198303224

Cited by 2 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The following compounds were prepared according to literature procedures: combretastatin A-4, 4d 1-(2-chloroethyl)-1H-pyrrole, 31 1-(2-chloroethyl)-1H-imidazole hydrochloride, 32 2-(2-chloroethyl)pyridine, 33 3-(2-chloroethyl)pyridine hydrochloride, 34 2-diethylaminoethyl chloride hydrochloride, 35 4-methoxy-3-nitrobenzaldehyde, 36 [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ether, 20 4-[(tert-butyldimethylsilyl)oxy]-3,5-dimethoxybenzaldehyde, 10j 3-(3-hydroxypropoxy)-4-methoxybenzaldehyde, 37 [3-(tert-butyldimethylsilyl)oxy]-4-methoxybenzyltriphenylphosphonium bromide, 38 3,4,5-trimethoxybenzyltriphenylphosphonium bromide, 12 N-(chloroformyl)bis-(2-chloroethyl)amine, 39 and 3-dimethylamino-4-methoxybenzaldehyde (7). 40 All other chemicals were purchased from either Acros Organics or Sigma-Aldrich Chemical Co.…”

Section: Methodsmentioning

confidence: 99%

Antineoplastic Agents. 445. Synthesis and Evaluation of Structural Modifications of (Z)- and (E)-Combretastatin A-4

et al. 2005

View full text Add to dashboard Cite

A series of cis- and trans-stilbenes related to combretastatin A-4 (1a), with a variety of substituents at the 3'-position of the aryl B-ring, were synthesized and evaluated for inhibitory activity employing six human cancer cell lines (NCI-H460 lung carcinoma, BXPC-3 pancreas, SK-N-SH neuroblastoma, SW1736 thyroid, DU-145 prostate, and FADU pharynx-squamous sarcoma) as well as the P-388 murine lymphocyte leukemia cell line. Several of the cis-stilbene derivatives were significantly inhibitory against all cell lines used, with potencies comparable to that of the parent 1a. All were potent inhibitors of tubulin polymerization. The corresponding trans-stilbenes had little or no activity as tubulin polymerization inhibitors and were relatively inactive against the seven cancer cell lines. In terms of inhibition of both cancer cell growth and tubulin polymerization, the dimethylamino and bromo cis-stilbenes were the most potent of the new derivatives, the latter having biological activity approaching that of 1a. As part of the present study, the X-ray crystal structure of the 3'-O-phosphate of combretastatin A-4 (1b) was successfully elucidated. Compound 1b has been termed the "combretastatin A-4 prodrug", and it is currently undergoing clinical trials for the treatment of human cancer patients.

show abstract

Section: Methodsmentioning

confidence: 99%

Antineoplastic Agents. 445. Synthesis and Evaluation of Structural Modifications of (Z)- and (E)-Combretastatin A-4

et al. 2005

View full text Add to dashboard Cite

show abstract

“…Obtained from 1-(2-chloroethyl)-1 H -pyrrole as a white solid after purification by flash chromatography (silica gel/PE/EtOAc 95/5) (30% yield, mp 127.7–129.0 °C). 1 H NMR (CDCl 3 ): δ 1.11 (3H, t, J = 7.35 Hz, OCH 2 CH 2 C H 3 ), 1.84–1.94 (2H, m, OCH 2 C H 2 CH 3 ), 4.04 (2H, t, J = 6.61 Hz, OCH 2 C H 2 N), 4.53 (4H, m, OC H 2 CH 2 N and OC H 2 CH 2 CH 3 );6.25 (2H, d, J = 2.11 Hz, pyrrole C H ), 6.89 (2H, t, J = 2.10 Hz, pyrrole NC H ), 7.04–7.09 (3H, m, H-3, H-3′ and H-5′), 7.52 (1H, t, J = 2.55 Hz, H-6), 7.73 (1H, t. J = 2.57 Hz, H-7), 8.05–8.13 (3H, m, H-8, H-2′ and H-6′), 8.20 (1H, d, J = 7.20 Hz, H-5).…”

Section: Experimental Sectionmentioning

confidence: 99%

“…To obtain compound 3c, the 1-(2-chloroethyl)pyrrole chain has been synthesized following the procedure reported in literature 55 starting from 2,5-bis(methyloxy)tetrahydrofuran and 2-chloroethylamine hydrochloride.…”

Section: ■ Chemistrymentioning

confidence: 99%

Re-evolution of the 2-Phenylquinolines: Ligand-Based Design, Synthesis, and Biological Evaluation of a Potent New Class of Staphylococcus aureus NorA Efflux Pump Inhibitors to Combat Antimicrobial Resistance

et al. 2013

View full text Add to dashboard Cite

Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of antimicrobial agents that are substrates. NorA is a Staphylococcus aureus efflux pump that confers reduced susceptibility to many structurally unrelated agents, including fluoroquinolones, biocides, and dyes, resulting in a multidrug resistant (MDR) phenotype. In this work, a series of 2-phenylquinoline derivatives was designed by means of ligand-based pharmacophore modeling in an attempt to identify improved S. aureus NorA efflux pump inhibitors (EPIs). Most of the 2-phenylquinoline derivatives displayed potent EPI activity against the norA overexpressing strain SA-1199B. The antibacterial activity of ciprofloxacin, when used in combination with some of the synthesized compounds, was completely restored in SA-1199B and SA-K2378, a strain overexpressing norA from a multicopy plasmid. Compounds 3m and 3q also showed potent synergistic activity with the ethidium bromide dye in a strain overexpressing the MepA MDR efflux pump.

show abstract

ChemInform Abstract: SYNTHESIS OF 1,2‐DIHYDRO‐3H‐PYRROLO(1,2‐A)PYRROLE‐1‐CARBOXYLIC ACIDS AND HOMOLOGOUS PYRIDINE AND AZEPINE ANALOGS THEREOF

Cited by 2 publications

References 1 publication

Antineoplastic Agents. 445. Synthesis and Evaluation of Structural Modifications of (Z)- and (E)-Combretastatin A-4

Antineoplastic Agents. 445. Synthesis and Evaluation of Structural Modifications of (Z)- and (E)-Combretastatin A-4

Re-evolution of the 2-Phenylquinolines: Ligand-Based Design, Synthesis, and Biological Evaluation of a Potent New Class of Staphylococcus aureus NorA Efflux Pump Inhibitors to Combat Antimicrobial Resistance

Contact Info

Product

Resources

About