Synthesis and Crystal Structure of Ethyl 7-Chloro-3-Amino-9-(4-Bromophenyl)Thieno-[3,2-b]Benzothiazine 4,4-Dioxide 2-Carboxylate

Charris, Jaime; Barazarte, Arthur; Ferrer, Rosa; Camacho, J.R.; Gamboa, Neira; Rodrígues, Juan; Atencio, Reinaldo; González, Teresa

doi:10.3184/030823407780199504

Cited by 5 publications

(6 citation statements)

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“…For related literature, see: Allen (2002); Allen et al (1987); Barazarte et al (2008); Capparelli et al (2008); Charris et al (2005Charris et al ( , 2007; Gilli et al (1989); Hirshfeld (1976); Kennard et al (2003); Krivokolysko et al (2002); Song et al (2005); Tominaga et al (1989Tominaga et al ( , 2002. Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound (II), and the 3′′-methoxy analogue (I) [see previous paper: Capparelli et al, 2008)], and similar derivatives, have been used as effective synthons in the syntheses of some 1H-pyrrole-2,5-diones (Tominaga et al, 2002), pyrimidine derivatives (Tominaga et al, 1989) and 4H-1,4-benzothiazine-1,1-dioxides (Charris et al, 2005). We used (I) and (II) as starting materials to develop benzothiazine derivatives with antimalarial activity (Charris et al, 2007;Barazarte et al, 2008).…”

Section: S1 Commentmentioning

confidence: 99%

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(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(4-methylanilino)-3-(methylsulfanyl)acrylonitrile

2008

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The title compound, C17H14Cl2N2O2S2, and the 3-methoxyanilino analogue reported in the preceding paper have been used as starting materials to develop benzothiazine derivatives with antimalarial activity. The molecule displays an E (trans) configuration about the central double bond. Due to conjugation in the C=C—C N group, the putative single bond shows a significant shortening [1.418 (3) Å]. The molecule has a six-membered ring involving an intramolecular N—H⋯O(sulfonyl) bond, which is an example of resonance-assisted hydrogen bonding. In the crystal structure, bonds of the C—H⋯O(sulfonyl) and C—H⋯N(cyano) types form double layers of molecules parallel to (01). Within these layers there are π–π interactions between benzene rings of pairs of centrosymmetrically related molecules, with distances of 3.7969 (12) Å between centroids. C—H⋯π interactions are also present.

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(4-methylanilino)-3-(methylsulfanyl)acrylonitrile

2008

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“…For related literature, see: Allen (2002); Allen et al (1987); Barazarte et al (2008); Capparelli et al (2008); Charris et al (2005Charris et al ( , 2007; Gilli et al (1989); Kennard et al (2003); Krivokolysko et al (2002); Song et al (2005); Tominaga et al (1989Tominaga et al ( , 2002.…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound (I), the 4′′-methyl analogue (II) [see next paper: Capparelli et al, 2008)], and similar derivatives, have been used as effective synthons in the syntheses of some 1Hpyrrole-2,5-diones (Tominaga et al, 2002), pyrimidine derivatives (Tominaga et al, 1989) and 4H-1,4-benzothiazine-1,1dioxides (Charris et al, 2005). We used (I) and (II) as starting materials to develop benzothiazine derivatives with antimalarial activity (Charris et al, 2007;Barazarte et al, 2008).…”

Section: S1 Commentmentioning

confidence: 99%

(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(3-methoxyanilino)-3-(methylsulfanyl)acrylonitrile

2008

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The title compound, C17H14Cl2N2O3S2, and the 4-methylanilino analogue reported in the following paper have been used as starting materials to develop benzothiazine derivatives with antimalarial activity. The molecule displays an E (trans) configuration about the central double bond. Due to conjugation in the C=C—C N group, the putative single bond shows a significant shortening [1.421 (3) Å]. The molecule has a six-membered ring involving an intramolecular N—H⋯O(sulfonyl) bond, which is an example of resonance-assisted hydrogen bonding. There is also an intramolecular N—H⋯Cl hydrogen bond. In the crystal structure, bonds of the C—H⋯O(sulfonyl) type form chains that run along [101], while N—H⋯O(sulfonyl) bonds connect centrosymmetrically related molecules in pairs of these chains, forming ribbons. Comparison of the N⋯O distances in the intra- and intermolecular N—H⋯O(sulfonyl) bonds reveals that the π-bond co-operativity results in a strengthening of the intramolecular hydrogen bond. There are also π–π interactions between benzene rings of pairs of centrosymmetrically related molecules [centroid–centroid distance = 3.8612 (13) Å], as well as C—H⋯π interactions.

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“…[3][4][5] more effective, antimalarial drugs, a number of quinoline, quinolone, pyrimidone, pyridopyrimidone, thiocromone, pyrazole and benzothiazine derivatives were synthesised, characterised and tested for antimalarial activity. [6][7][8][9][10][11][12][13][14][15] 3-Amino-7-chloro-9-phenyl-1,9H-pyrazolo- [4,3-b] Compounds 1 and 2 were synthesised as reported elsewhere. 16,17 Crystals suitable for X-ray diffraction were obtained by the slow evaporation of solution in EtOH.…”

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Crystal structures of two N-phenylated tricyclic benzothiazines with antimalarial activity

Barazarte

Gamboa

Rodrígues

et al. 2009

Journal of Chemical Research

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The crystal structures of two N-phenylated tricyclic benzothiazines were determined 3-amino-7-chloro-9-phenyl-1,9H-pyrazolo-[4,3-b] benzothiazine 4,4-dioxide, C 15 H 11 ClN 4 O 2 S crystallises in P2 1 /c with a = 11.436 (4)Å, b = 10.894 (3)Å, c = 11.858 (4)Å, = 95.297 (9)°, V = 1471.0 (8) Å 3 and Z = 4, while 2,4-diamino-8-chloro-10H-phenylpyrimido-[5,4b]benzothiazine 5,5-dioxide, C 16 H 12 ClN 5 O 2 S crystallises in P2 1 /c with a = 7.496 (2)Å, b = 17.728 (4)Å, c = 11.889 (2)Å, = 91.524 ( 5)°, V = 1579.4 (5)Å 3 and Z = 4. Both molecules are essentially planar, including the exocyclic groups. These compounds were promising as inhibitors of hemoglobin hydrolysis, however, their effect as inhibitors of -hematin formation was marginal. The most active compound to emerge from the in vitro and in vivo murine studies was the pyrimidobezothaizine, suggesting an antimalarial activity via inhibition of haemoglobin hydrolysis, but it was not as efficient as chloroquine.

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Synthesis and Crystal Structure of Ethyl 7-Chloro-3-Amino-9-(4-Bromophenyl)Thieno-[3,2-b]Benzothiazine 4,4-Dioxide 2-Carboxylate

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Cited by 5 publications

References 7 publications

(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(4-methylanilino)-3-(methylsulfanyl)acrylonitrile

(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(4-methylanilino)-3-(methylsulfanyl)acrylonitrile

(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(3-methoxyanilino)-3-(methylsulfanyl)acrylonitrile

Crystal structures of two N-phenylated tricyclic benzothiazines with antimalarial activity

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