Synthesis, crystal structure, and rotational energy profile of 3-cyclopropyl-1,2,4-benzotriazine 1,4-di-n-oxide

Journal of Chemical Crystallography

Volumn 40, Issue 7, 2010, Pages 624-629

  Sarkar, Ujjal ^a   Glaser, Rainer ^a   Parsons, Zack D ^a   Barnes, Charles L ^a   Gates, Kent S ^a,b  

^a UNIVERSITY OF MISSOURI   (United States)

^b University of Missouri   (United States)

Author keywords

Crystal structure; Cyclopropyl group; N oxide; Rotational energy profile; Tirapazamine

Indexed keywords

EID: 77956733676     PISSN: 10741542     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10870-010-9707-9     Document Type: Article

References (31)

1. Marco L, Olver I (2006) Curr Clin Oncol 1:71-79
2. Le Q-TX, Moon J, Redman M, Williamson SK, Lara PN Jr, Goldberg Z, Gaspar LE, Crowley JJ, Moore DF Jr, Gandara DR (2009) J Clin Oncol 27:3014-3019
3. Horsman MR (1998) Int J Radiat Oncol Biol Phys 42:701-704
4. Siemann DW (1998) Int J Radiat Oncol Biol Phys 42:697-699
5. Vaupel P, Kallinowski F, Okunieff P (1989) Cancer Res 49: 6449-6465
6. Brown JM, Wilson WR (2004) Nat Rev Cancer 4:437-447
7. Brown JM (1999) Cancer Res 59:5863-5870
8. Zeman EM, Brown JM, Lemmon MJ, Hirst VK, Lee WW (1986) Int J Radiat Oncol Biol Phys 12:1239-1242
9. Hay MP, Hicks KO, Pruijn FB, Pchalek K, Siim BG, Wilson WR, Denny WAJ (2007) Med Chem 50:6392-6404
10. Hay MP, Pchalek K, Pruijn FB, Hicks KO, Siim BG, Anderson RF, Shinde SS, Phillips V, Denny WA, Wilson WRJ (2007) Med Chem 50:6654-6664
11. Chowdhury G, Junnutula V, Daniels JS, Greenberg MM, Gates KSJ (2007) Am Chem Soc 129:12870-12877
12. Birincioglu M, Jaruga P, Chowdhury G, Rodriguez H, Dizdaroglu M, Gates KSJ (2003) Am Chem Soc 125:11607-11615
13. Kotandeniya D, Ganley B, Gates KS (2002) Bioorg Med Chem Lett 12:2325-2329
14. Daniels JS, Gates KS, Tronche C, Greenberg MM (1998) Chem Res Toxicol 11:1254-1257
15. Junnotula V, Sarkar U, Sinha S, Gates KSJ (2009) Am Chem Soc 130:1015-1024
16. Daniels JS, Gates KSJ (1996) Am Chem Soc 118:3380-3385
17. Anderson RF, Shinde SS, Hay MP, Gamage SA, Denny WAJ (2003) Am Chem Soc 125:748-756
18. Shinde SS, Hay MP, Patterson AV, Denny WA, Anderson RF (2009) J Am Chem Soc 131:14220-14221
19. Sheldrick GM (1997) SHELXS-97, program for the solution 125 of crystal structures. University of Gottingen, Germany
20. Sheldrick GM (1997) SHELXS-97, program for the refinement 128 of crystal structures. University of Gottingen, Germany
21. Fuchs T, Gates KS, Hwang J-T, Greenberg MM (1999) Chem Res Toxicol 12:1190-1194
22. de Boer JSAM, Loopstra BO, Stam CH (1987) Red Trau Chim Pays-Bas 106:537
23. Shen Q, Wells C, Traetteberg M, Bohn RK, Willis A, Knee J (2001) J Org Chem 66:5840-5845
24. Bernal I, Levendis DC, Fuchs R, Reisner GM, Cassidy JM (1997) Struct Chem 84:275-285
25. Drumright RE, Mas RH, Merola JS, Tanko JMJ (1990) Org Chem 55:4098-4102
26. Traetteberg M, Rauch K, de Meijere A (2005) J Mol Struct 738:25-31
27. Cramer CJ (2004) Essentials of computational chemistry. New York, Wiley
28. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, revision D.01. Gaussian Inc., Wallingford
29. Cheeseman JR, Trucks GW, Keith TA, Frisch MJJ (1996) Chem Phys 104:5497-5509
30. Alkorta I, Elguero J (2003) Struct Chem 14:377-389
31. Deng W, Cheeseman JR, Frisch MJ (2006) J Chem Theory Comput 2:1028-1037