Synthesis and Chemical Transformations of 6‐(Morpholine‐4‐sulfonyl)‐quinoline‐2,3,4‐tricarboxylic Acid.

Кравченко, Д. В.; Kysil, Volodymyr; Ilyn, Alexey P.; Ткаченко, С. Е.; Maliarchouk, Sergey; Okun, Ilya; Ivachtchenko, Alexandre V.

doi:10.1002/chin.200635152

Cited by 21 publications

(33 citation statements)

References 1 publication

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“…Scheme 23 shows an example of a Suzuki phenylation that was employed to extend the P2 side chain of dipeptidyl ni-triles with an aminoacetonitrile group at P1 serving as the electrophile [86]. Very recently an efficient microwavepromoted copper-catalyzed cyanation was conducted from a quinolinyl bromide to provide a caspase-3 inhibitor (52) with an IC 50 value of 16 nM [87]. This cyanation reaction constitutes an excellent complement to the palladium-catalyzed version.…”

Section: Serine and Cysteine Protease Inhibitorsmentioning

confidence: 98%

Controlled Microwave Heating as an Enabling Technology: Expedient Synthesis of Protease Inhibitors in Perspective

2007

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Since the early days of organic chemistry, oil baths, hot plates, metal blocks, and isomantles have been the heating devices of choice for driving chemical reactions. Over the last years, microwave heating has evolved as a well-demonstrated alternative to classic heating with the potential to emerge as the preferred heating method in organic synthesis. In this perspective, we will illustrate that microwave heating has an edge over conventional heating also in medicinal and high-throughput chemistry applications, enabling both an expanded reaction range and the diminishing of reaction times from many hours or days down to minutes. By focusing on the development of protease inhibitors, we present a series of successful lead optimizations starting from complex core structures and using controlled microwave heating as the energy source. In short, hundreds of protease inhibitors have been quickly synthesized under microwave irradiation since the start of our high-speed program back in 1998.

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Section: Serine and Cysteine Protease Inhibitorsmentioning

confidence: 98%

Controlled Microwave Heating as an Enabling Technology: Expedient Synthesis of Protease Inhibitors in Perspective

2007

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“…For background to pyrrolidine derivatives, see: Grigg (1995); Kravchenko et al (2005). For ring conformation analysis, see : Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

“…Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97. Pyrrolidine-containing compounds are of significant importance because of their biological activities and widespread employment in catalysis (Grigg, 1995;Kravchenko et al, 2005). As part of our own studies in this area, we have undertaken the crystal structure determination of the title compound, a pyrrolidine derivative,and the results are presented here.…”

Section: Data Collectionmentioning

confidence: 99%

(3aR,8bR)-3a,8b-Dihydroxy-2-methylsulfanyl-3-nitro-1-phenyl-1,8b-dihydroindeno[1,2-b]pyrrol-4(3aH)-one

Nagalakshmi¹,

Suresh²,

Jeyachandran

et al. 2013

Acta Cryst E

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In the title compound, C18H14N2O5, the pyrrolidine ring adopts a shallow envelope conformation, with the C atom bearing the OH group (and remote from the N atom) displaced by 0.257 (2) Å from the other atoms. The cyclopentane ring has a twisted conformation about the C—C bond bearing one =O and one —OH grouping. The dihedral angle between the five-membered rings (all atoms) is 65.54 (9)° and the OH groups lie to the same side of the ring-junction. The molecular structure features a weak intramolecular O—H...O bond and a possible C—H...π interaction. In the crystal, the molecules are linked into [010] chains by O—H...O hydrogen bonds. Weak C—H...O bonds connect the chains into (100) sheets.

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“…It represents a novel scaffold for non-peptide inhibitors of executioner caspases. A number of derivatives varying at the R1, R2 and R3 positions were synthesized and evaluated in caspase-3 in vitro inhibition assays [52][53][54][55]. Compound 6 with the combination of a morpholinesulfonyl moiety at position R1 and 1,3,5-trimethyl-1H-pyrazol-4-yl group at R2 was the lead compound among those tested when R3 was fixed to -CH 3 (Fig.…”

Section: Quinoline Derivativesmentioning

confidence: 99%

Caspases: Structure-Guided Design of Drugs to Control Cell Death

Weber

Fang²,

Agniswamy³

2008

MRMC

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The structures of caspases reveal the mechanism of binding for non-peptide and protein inhibitors, and have been applied in the design of agents that either inhibit or activate caspases to control cell death in diverse diseases. Decreased cell death is desirable for treatment of stroke, nerve crush injury, myocardial infarction, neuromuscular and neurodegenerative diseases and several non-peptide caspase inhibitors have been developed. In contrast, activation of cell death would be advantageous in cancer therapy, and the strategy is to block the binding of inhibitory proteins to caspases. Recent preclinical studies are described.

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Synthesis and Chemical Transformations of 6‐(Morpholine‐4‐sulfonyl)‐quinoline‐2,3,4‐tricarboxylic Acid.

Cited by 21 publications

References 1 publication

Controlled Microwave Heating as an Enabling Technology: Expedient Synthesis of Protease Inhibitors in Perspective

Controlled Microwave Heating as an Enabling Technology: Expedient Synthesis of Protease Inhibitors in Perspective

(3aR,8bR)-3a,8b-Dihydroxy-2-methylsulfanyl-3-nitro-1-phenyl-1,8b-dihydroindeno[1,2-b]pyrrol-4(3aH)-one

Caspases: Structure-Guided Design of Drugs to Control Cell Death

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