Synthesis and X-ray analysis of butyl and glycosyl (2-arylamino-4,4- dimethyl-6-oxocyclohex-1-ene)carbodithioates and their possible cyclization to 2-thioxo-6,7-dihydro-1H-benzo[d][1,3]thiazin-5(2H)-one derivatives

Carbohydrate Research

Volumn 346, Issue 2, 2011, Pages 169-176

  El Ashry, El Sayed H ^a,b   Aly, Aly A ^c   Amer, Mohammed R ^a   Shah, Muhammad R ^a   Ng, Seik W ^d  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b Alexandria University Faculty Of Science   (Egypt)

^c BENHA UNIVERSITY   (Egypt)

^d UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Benzothiazines; Carbodithioates; Dimedone; Enaminones; Thioglycosides; X ray

Indexed keywords

BENZOTHIAZINES; CARBODITHIOATES; DIMEDONE; ENAMINONES; THIOGLYCOSIDES;

BROMINE COMPOUNDS; CYCLIZATION; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY; X RAYS;

CARBON DISULFIDE;

(2',3',4',6' TETRA O ACETYL BETA GALACTOPYRANOSYL) [2 (2,4 DICHLOROPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE] CARBODITHIOIC ACID; (2',3',4',6' TETRA O ACETYL BETA GALACTOPYRANOSYL) [2 (4 BROMOPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE] CARBODITHIOIC ACID; (2',3',4',6' TETRA O ACETYL BETA GALACTOPYRANOSYL) [2 (4 CHLOROPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE] CARBODITHIOIC CID; (2',3',4',6' TETRA O ACETYL BETA GLUCOPYRANOSYL) [2 (2,4 DICHLOROPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE] CARBODITHIOIC ACID; (2',3',4',6' TETRA O ACETYL BETA GLUCOPYRANOSYL) [2 (4 BROMOPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE] CARBODITHIOIC ACID; (2',3',4',6' TETRA OACETYL BETA GLUCOPYRANOSYL) [2 (4 CHLOROPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE] CARBODITHIOIC ACID; 4 (BUTYLTHIO) 1 (2,4 DICHLOROPHENYL) 7,7 DIMETHYL 2 THIOXO 6,7 DIHYDRO 1H BENZO[D][1,3]THIAZIN 5(2H) ONE; 4 (BUTYLTHIO) 1 (4 BROMOPHENYL) 7,7 DIMETHYL 2 THIOXO 6,7 DIHYDRO 1H BENZO[D][1,3]THIAZIN 5(2) ONE; 4 (BUTYLTHIO) 1 (4 CHLOROPHENYL) 7,7 DIMETHYL 2 THIOXO 6,7 DIHYDRO 1H BENZO[D][1,3]THIAZIN 5(2H) ONE; BENZOTHIAZINE DERIVATIVE; CARBODITHIOIC ACID DERIVATIVE; CARBON DISULFIDE; DITHIOCARBAMIC ACID DERIVATIVE; N BUTYL [2 (2,4 DICHLOROPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE]CARBODITHIOIC ACID; N BUTYL [2 (4 BROMOPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE]CARBODITHIOIC ACID; N BUTYL [2 (4 CHLOROPHENYLAMINO) 4,4 DIMETHYL 6 OXOCYCLOHEX 1 ENE]CARBODITHIOIC ACID; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOHEXANONES; CYCLOHEXYLAMINES; THIOCARBAMATES; THIOGLYCOSIDES;

EID: 78651348673     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.11.005     Document Type: Article

References (79)

1. Z. Ur-Rehman, N. Muhammada, S. Shuja, S. Ali, I.S. Butler, A. Meetsma, and M. Khan Polyhedron 28 2009 3439 3448
2. P.J. Nieuwenhuizen, J. Reedijk, M. van Duin, and W.J. McGill Rubber Chem. Technol. 70 1997 368 429
3. D. Fan, M. Afzaal, M.A. Malik, C.Q. Nguyen, P. O'Brien, and P.J. Thomas Coord. Chem. Rev. 251 2007 1878 1888
4. E.R. Knight, A.R. Cowley, G. Hogarth, and J.D. Wilton-Ely Dalton Trans. 2009 607 609
5. A. Waseem, M. Yaqoob, and A. Nabi Anal. Sci. 2009 395 400
6. B. Cvek, and Z. Dvorak Curr. Pharm. Des. 13 2007 3155 3167
7. S. Shahzadi, S. Ali, M.H. Bhatti, M. Fettouhi, and M. Athar J. Organomet. Chem. 691 2006 1797 1802
8. P. Yang, and M. Guo Coord. Chem. Rev. 189 1999 185 186
9. R.K. Chadha, R. Kumar, and D.G. Tuck Can. J. Chem. 65 1987 1336 1342
10. T.A. Al-Allaf, I.A. Mustafa, and S.E. Al-Mukhtar Trans. Met. Chem. 18 1993 1 5
11. P.C. David, and M.C. Chrislyn Pestic. Sci. 23 2006 93 102
12. I. Rogachev, V. Kampel, V. Gusis, N. Cohen, J. Gressel, and A. Warshawasky Pestic. Biochem. Physiol. 60 1998 133 145
13. A. Ur-Rehman, M. Hussain, Z. Ur-Rehman, A. Rauf, F.H. Nasim, A.A. Tahir, and S. Ali J. Organomet. Chem. 695 2010 1526 1532
14. D. Boers, L. van Amelsvoort, C. Colosio, E. Corsini, S. Fustinoni, L. Campo, C. Bosetti, C. La Vecchia, T. Vergieva, M. Tarkowski, J. Liesivuori, P. Steerenberg, and H. van Loveren Hum. Exp. Toxicol. 27 2008 721 727
15. O.G. Zel, and A. Salman Bioorg. Med. Chem. 14 2006 7804 7815
16. M. Soledade, C. Pedras, and M. Jha Bioorg. Med. Chem. 14 2006 4958 4979
17. H.D. Yin, and S.C. Xue Appl. Organomet. Chem. 20 2006 283 289
18. S. Tabassum, and C. Pettinari J. Organomet. Chem. 691 2006 1761 1766
19. C. Pellerito, P. D'Agati, T. Fiore, C. Mansueto, V. Mansueto, G. Stocco, L. Nagy, and L. Pellerito J. Inorg. Biochem. 99 2005 1294 1305
20. V. Milacic, and Q.P. Dou Coord. Chem. Rev. 253 2009 1649 1660 pubmed/20047011
21. X. Zhang, M. Frezza, V. Milacic, L. Ronconi, Y. Fan, C. Bi, D. Fregona, and Q.P. Dou J. Cell. Biochem. 109 2010 162 172
22. S.P. Bach, R. Chinery, S.T. O'Dwyer, C.S. Potten, R.J. Coffey, and A.J. Watson Gastroenterology 118 2000 81 89
23. K.G. Daniel, D. Chen, S. Orlu, Q.C. Cui, F.R. Miller, and Q.P. Dou Breast Cancer Res. 7 2005 897 908
24. A. Trevisan, C. Marzano, P. Cristofori, M. Borella Venturini, L. Giovagnini, and D. Fregona Arch. Toxicol. 76 2002 262 268
25. W. Huang, Y. Ding, Y. Miao, M.-Z. Liu, Y. Li, and G.-F. Yang Eur. J. Med. Chem. 44 2009 3687 3696
26. X. Si, B.M. McManus, J. Zhang, J. Yuan, C. Cheung, M. Esfandiarei, A. Suarez, A. Morgan, and H. Luo J. Virol. 79 2005 8014 8023
27. M. Sofuoglu, and T.R. Kosten CNS Drugs 19 2005 13 25
28. I.M. Fang, C.H. Yang, C.P. Lin, C.M. Yang, and M.S. Chen Ocul. Pharmacol. Ther. 21 2005 95 106
29. D.W. Pyatt, J. Gruntmeir, W.S. Stillman, and R.D. Irons Toxicology 128 1998 83 90
30. U. Noboru, and O. Kunio J. Antimicrob. Chemother. 52 2003 8 10
31. N. Uchide, K. Ohyama, T. Bessho, B. Yuan, and T. Yamakawa Antiviral Res. 56 2002 207 217
32. V. Amarnath, K. Amarnath, and W.M. Valentine Curr. Top. Toxicol. 4 2007 39 44
33. P.K. Gogoi, D.P. Phukan, and D.K. Das Asian J. Chem. 11 1999 1291 1295
34. H.P.S. Chauhan, and N.M. Shaik J. Inorg. Biochem. 99 2005 538 545
35. G. Eng, X. Song, Q. Duong, D. Strickman, J. Glass, and L. May Appl. Organomet. Chem. 17 2003 218 225
36. O.M. Viquez, B. Lai, J.H. Ahn, M.D. Does, H.L. Valentine, and W.M. Valentine Toxicol. Appl. Pharmacol. 239 2009 71 79
37. X. Zhu, and R.R. Schmidt Angew. Chem., Int. Ed. 48 2009 1900 1934
38. K. Pachamuthu, and R.R. Schmidt Chem. Rev. 106 2006 160 187
39. R.R. Schmidt, J.C. Castro-Palomino, and O. Retz Pure Appl. Chem. 71 1999 729 744
40. R.R. Schmidt S.H. Khan, R.A. O'Neill, Modern Methods in Carbohydrate Synthesis 1996 Harwood Amsterdam 20 54
41. A.A.-H. Abdel-Rahman, E.S.H. El Ashry, and R.R. Schmidt Carbohydr. Res. 337 2002 195 206
42. P. Pornsuriyasak, U.B. Gangadharmath, N.P. Rath, and A. Demchenko Org. Lett. 6 2004 4515 4518 doi/abs/10.1021/ol048043y
43. A.V. Demchenko, M.N. Kamat, and C. De Meo Synlett 2003 1287 1290
44. A.V. Demchenko, P. Pornsuriyasak, C. De Meo, and N.N. Malysheva Angew. Chem., Int. Ed. 43 2004 3069 3072
45. U.B. Gangadharmath, and A.V. Demchenko Synlett 2004 2191 2193
46. A.V. Demchenko, N.N. Malysheva, and C. De Meo Org. Lett. 5 2003 455 458
47. E.S.H. El Ashry, N. Rashed, and E.I. Ibrahim Tetrahedron 64 2008 10631 10648
48. E.S.H. El Ashry, N. Rashed, and E.I. Ibrahim Curr. Org. Synth. 2 2005 175 213
49. E.S.H. El Ashry, and M.R.E. Aly Pure Appl. Chem. 79 2007 2229 2242
50. E.S.H. El Ashry, L.F. Awad, and I.A. Atta Tetrahedron 62 2006 2943 2998
51. N. Rezki, N. Rashed, L.F. Awad, E. Ramadan, S.M. Abdel-Maggeed, and E.S.H. El Ashry Phosphorus, Sulfur Silicon Relat. Elem. 184 2009 1759 1767
52. O.M.E. Awad, W.E. Attia, and E.S.H. El Ashry Carbohydr. Res. 339 2004 469 476
53. E.S.H. El Ashry, L.F. Awad, H. Abdel-Hamid, and I.A. Atta J. Carbohydr. Chem. 24 2005 745 753
54. E.S.H. El Ashry, N. Rashed, and A.H. Shobier Pharmazie 55 2000 251 262
55. E.S.H. El Ashry, N. Rashed, and A.H. Shobier Pharmazie 55 2000 331 348
56. E.S.H. El Ashry, N. Rashed, and A.H. Shobier Pharmazie 55 2000 403 415
57. E.S.H. El Ashry, and A. El Nemr Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates 2005 Blackwell Oxford
58. A.A. Aly Phosphorus, Sulfur, Silicon Relat. Elem. 178 2003 2415 2429
59. P. Fuegedi, P.J. Garegg, S. Oscarson, G. Rosen, and B.A. Silwanis Carbohydr. Res. 211 1991 157 162
60. G.H. Elgemeie, W.A. Zaghary, T.M. Nasr, and K.M. Amin J. Carbohydr. Chem. 27 2008 345 356
61. J. Bogusiak, and W. Szeja Tetrahedron Lett. 42 2001 2221 2223
62. M.S. Behalo, and A.A. Aly J. Chem. Res., Synop. 12 2009 753 755
63. J. Bogusiak, and W. Szeja Carbohydr. Res. 330 2001 141 144
64. I. Wandzik, and W. Szeja Pol. J. Chem. 73 1999 1163 1170
65. J. Bogusiak, and W. Szeja Carbohydr. Res. 295 1996 235 243
66. S. Tejima, and S. Ishiguro Chem. Pharm. Bull. 15 1967 255 263
67. L. Byung-Hoon, B. Barbara, S. Peter, F. Norbert, and W. Manfred J. Med. Chem. 37 1994 3154 3162
68. G.M. Pieper, W. Siebeneich, C.L. Olds, and C.-S. Lai Eur. J. Pharmacol. 472 2003 127 134
69. E.S.H. El Ashry, M.R. Amer, M.R. Shah, and S.W. Ng Acta Crystallogr., Sect. E 65 2009 o1106
70. E.S.H. El Ashry, M.R. Amer, M.R. Shah, and S.W. Ng Acta Crystallogr., Sect. E 65 2009 o597
71. E.S.H. El Ashry, M.R. Amer, M.R. Shah, and S.W. Ng Acta Crystallogr., Sect. E 65 2009 o599
72. E.S.H. El Ashry, M.R. Amer, M.R. Shah, and S.W. Ng Acta Crystallogr., Sect. E 65 2009 o600
73. T. Yamasaki, K. Nishida, T. Okawara, and M. Furukawa Heterocycles 47 1998 315 327
74. Y. Tominaga, H. Okuda, S. Kohra, and H. Mazume J. Heterocycl. Chem. 28 1991 1245 1255
75. L.J. Barbour J. Supramol. Chem. 1 2001 189 191
76. Bruker, APEX2 software (v2008.6-1) and saint (Version 7.60A); Bruker AXS Inc.: Madison, WI, USA, 2008.
77. H.D. Flack Acta Crystallogr., Sect. A 39 1983 876 881
78. Sheldrick, G. M. sadabs. Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Germany, 1996.
79. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112 122