Easily synthesized antimalarial ferrocene triazacyclononane quinoline conjugates

Biot, Christophe; Dessolin, Jean; Ricard, Isabelle; Dive, Daniel

doi:10.1016/j.jorganchem.2004.04.036

Cited by 51 publications

(39 citation statements)

References 22 publications

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“…Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 (Biot et al, 2004), antitumor (Jaouen et al, 2004), and antibacterial (Fouda et al, 2007). Against this background, and in order to obtain information on the molecular conformation of such compounds, we synthesised the title compound and report herein on its crystal structure.…”

Section: Methodsmentioning

confidence: 99%

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6-Ferrocenoyl-7-phenylspiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11′-indeno[1,2-b]quinoxaline]

et al. 2013

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.003 Å; R factor = 0.034; wR factor = 0.094; data-to-parameter ratio = 15.2.In the title compound, [Fe(C 5 H 5 )(C 32 H 24 N 3 OS)], both the thiazolidine ring and the pyrrolidine ring adopt an envelope conformation, with the S atom and the phenyl-bearing C atom, respectively, as the flaps. The thiazolidine ring mean plane makes a dihedral angle of 59.08 (11) with the pyrrolidine ring mean plane, which in turn makes a dihedral angle of 83.40 (10) with the cyclopentane ring, indicating that the latter two rings are almost orthogonal to one another. In the crystal, a pair of C-HÁ Á ÁO hydrogen bonds link the molecules forming inversion dimers. The dimers are linked viainteractions [centroid-centroid distance = 3.7764 (10) Å ] involving the quinoxaline moieties forming chains propagating along [110]. Related literature

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Section: Methodsmentioning

confidence: 99%

“…For the biological activity of ferrocene derivatives, see : Jaouen et al (2004); Biot et al (2004); Fouda et al (2007). For a related structure, see: Vijayakumar et al (2012).…”

Section: Related Literaturementioning

confidence: 99%

6-Ferrocenoyl-7-phenylspiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11′-indeno[1,2-b]quinoxaline]

et al. 2013

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“…The 7-substituted 4-aminoquinoline moiety and length of the methylene spacer were major determinants for antimalarial activity [134] . For ferrocene triazacyclononane quinoline conjugate 52 [135] against the Dd2 strain, the IC 50 was 62±12 nmol·L −1 , this showed that 52 was more efficient than chloroquine (IC 50 = 94±8 nmol·L −1 ), but less active than ferroquine (IC 50 = 13±1 nmol·L −1 ). These results showed the potential of ferrocenic bisquinolines complex 52 as antimalarial agents.…”

Section: Supermolecules As Antimalarial Agentsmentioning

confidence: 96%

Review on supermolecules as chemical drugs

Zhou

Gan

Zhang

et al. 2009

Sci. China Ser. B-Chem.

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Supramolecular medicinal chemistry field has been a quite rapidly developing, increasingly active and newly rising interdiscipline which is the new expansion of supramolecular chemistry in pharmaceutical sciences, and is gradually becoming a relatively independent scientific area. Supramolecular drugs could be defined as medicinal supermolecules formed by two or more molecules through noncovalent bonds. So far a lot of supermolecules as chemical drugs have been widely used in clinics. Supermolecules as chemical drugs, i.e. supramolecular chemical drugs or supramolecular drugs, which might have the excellences of lower cost, shorter period, higher potential as clinical drugs for their successful research and development, may possess higher bioavailability, better biocompatibility and drug-targeting, fewer multidrug-resistances, lower toxicity, less adverse effect, and better curative effects as well as safety, and therefore exhibit wide potential application. These overwhelming advantages have drawn enormous special attention. This paper gives the definition of supramolecular drugs, proposes the concept of supramolecular chemical drugs, and systematically reviews the recent advances in the research and development of supermolecules, including organic and inorganic complex ones as chemical drugs in the area of antitumor, anti-inflammatory, analgesic, antimalarial, antibacterial, antifungal, antivirus, anti-epileptic, cardiovascular agents and magnetic resonance imaging agents and so on. The perspectives of the foreseeable future and potential application of supramolecules as chemical drugs are also presented.

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“…For the biological activity of ferrocene derivatives, see: Jaouen et al (2004); Biot et al (2004);Fouda et al (2007). For related structures, see: Satis Kumar et al(2007); Kamala et al (2009); Gunasekaran et al (2010); For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).…”

Section: Related Literaturementioning

confidence: 99%

3-(Ferrocen-1-ylcarbonyl)-1-methyl-4-(4-methylphenyl)spiro[pyrrolidine-2,11′-indeno[1,2-b]quinoxaline]

Balakrishnan¹,

Gavaskar²,

Srinivasan³

et al. 2012

Acta Cryst E

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In the title compound, [Fe(C5H5)(C32H26N3O)], the pyrrolidine ring adopts a twist conformation. The indeno–quinoxaline ring system [86.44 (5)°], the methylphenyl ring [86.06 (7)°] and the ferrocene rings [82.00 (7) and 83.95 (9)°] are almost perpendicular to the pyrrolidine ring. The two cyclopentadienyl rings adopt an eclipsed conformation. The crystal structure features C—H⋯N interactions.

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Easily synthesized antimalarial ferrocene triazacyclononane quinoline conjugates

Cited by 51 publications

References 22 publications

6-Ferrocenoyl-7-phenylspiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11′-indeno[1,2-b]quinoxaline]

6-Ferrocenoyl-7-phenylspiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11′-indeno[1,2-b]quinoxaline]

Review on supermolecules as chemical drugs

3-(Ferrocen-1-ylcarbonyl)-1-methyl-4-(4-methylphenyl)spiro[pyrrolidine-2,11′-indeno[1,2-b]quinoxaline]

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