Cyclobutane-derived diamines: Synthesis and molecular structure

Journal of Organic Chemistry

Volumn 75, Issue 17, 2010, Pages 5941-5952

  Radchenko, Dmytro S ^a,b   Pavlenko, Sergiy O ^a,b   Grygorenko, Oleksandr O ^a,b   Volochnyuk, Dmitriy M ^b,c   Shishkina, Svitlana V ^c   Shishkin, Oleg V ^c   Komarov, Igor V ^a,b  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b ENAMINE LTD   (Ukraine)

^c INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; CONFORMATIONAL PREFERENCES; CYCLOBUTANE RING; CYCLOBUTANES; DRUG DISCOVERY; LITERATURE DATA; MALONATES;

HEPTANE; X RAY DIFFRACTION;

BUTANE;

3,6 DIAMINOSPIRO[3.3]HEPTANE; 6 AMINO 3 AZASPIRO[3.3]HEPTANE; ARIPIPRAZOLE; ASTEMIZOLE; CIS 1,3 DIAMINOCYCLOBUTANE; CYCLOBUTANE; DEMETHOXYCISAPRIDE; DIAMINE DERIVATIVE; GRANISETRON; MALONIC ACID; MARAVIROC; TRANS 1,3 DIAMINOCYCLOBUTANE; TROPAPRIDE; TROVAFLOXACIN; UNCLASSIFIED DRUG; ZOPICLONE;

ALKYLATION; AMINATION; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; SYNTHESIS; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; CYCLOBUTANES; DIAMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77956136781     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101271h     Document Type: Article

References (66)

1. Mann, A. In Practice of Medicinal Chemistry, 3rd ed.; Wermuth, C. G., Ed.; Academic Press/Elsevier: Amsterdam, The Netherlands, 2008; pp 363 - 379.
2. Feher, M.; Schmidt, J. M. J. Chem. Inf. Comput. Sci. 2003, 43, 218-227
3. Martin, S. F. Pure Appl. Chem. 2007, 79, 193-200
4. MDL Drug Data Report (MDDR); Elsevier MDL, version 2009.2
5. Barril, X.; Solvia, R. In Structure-Based Drug Discovery: An Overview; Hubbard, R. E., Ed.; RSC Publishing: Cambridge, UK, 2006; pp 54 - 96.
6. Cowell, S. M.; Lee, Y. S.; Cain, J. P.; Hruby, V. J. Curr. Med. Chem. 2004, 11, 2785-2798
7. Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249-262
8. Shemyakin, M. M.; Ovchinnikov, Y. A.; Ivanov, V. T. Angew. Chem., Int. Ed. 1969, 8, 492-499
9. Komarov, I. V.; Grigorenko, A. O.; Turov, A. V.; Khilya, V. P. Russ. Chem. Rev. 2004, 73, 785-810
10. Soloshonok, V. A. Curr. Org. Chem. 2002, 6, 341-364
11. Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145-148
12. Soloshonok, V. A.; Tang, X. J.; Hruby, V. J.; Meervelt, L. V. Org. Lett. 2001, 3, 341-343
13. Kotti, S. R. S. S.; Timmons, C.; Li, G. Chem. Biol. Drug. Des. 2006, 67, 101-114
14. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627
15. Levy, J. A. AIDS 2009, 23, 147-160
16. Yarker, Y. E.; McTavish, D. Drugs 1994, 48, 761-793
17. Krishnamoorthy, S.; Lip, G. Y. Expert Opin. Invest. Drugs 2009, 18, 1191-1196
18. Salaun, J. Chem. Rev. 1989, 89, 1247-1270
19. A. Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625-1648
20. de Meijere, A. Chem. Rev. 2003, 103, 931-932
21. Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511-542
22. Salaün, J. In Small Ring Compounds in Organic Synthesis VI; de Meijere, A.; Kozhushkov, S. I., Eds.; Springer: Berlin/Heidelberg, Germany, 2000; pp 1 - 67.
23. Sergeiko, A.; Poroikov, V. V.; Hanus, L. O.; Dembitsky, V. M. Open Med. Chem. J. 2008, 2, 26-37
24. Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485-1538
25. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 1267.
26. Avram, M.; Nenitzescu, C. D.; Maxim, M. Chem. Ber. 1957, 90, 1424-1427
27. Engelhardt, H.; Stadtmueller, H.; Steegmaier, M. PCT Int. Pat. WO 2007115999, 2007.
28. Helal, C. J.; Kang, Z.; Lucas, J. C.; Bohall, B. R. Org. Lett. 2004, 6, 1853-1856
29. Ahlijanian, M. K.; Cooper, C. B.; Helal, C. J.; Lau, L.-F.; Menniti, F.; Sanner, M. A.; Seymour, P. A.; Villalobos, A. PCT Int. Pat. WO 0210141, 2002.
30. Stadtmueller, H.; Engelhardt, H.; Steegmaier, M.; Baum, A.; Guertler, U.; Schoop, A.; Quant, J. J.; Solca, F.; Hauptmann, R.; Reiser, U.; Zahn, S. K.; Herfurth, L. PCT Int. Pat. WO 2006021544, 2006.
31. Kuang, R.; Blythin, D.; Shih, N.-Y.; Shue, H.-J.; Chen, X.; Cao, J.; Gu, D.; Huang, Y.; Schwerdt, J. H.; Ting, P. C.; Wong, S.-C; Xiao, L. PCT Int. Pat. WO 2005116009, 2005.
32. Lowe, J. A.; Sakya, S. M.; Sanner, M., A.; Coe, J. W.; McHardy, S. F. PCT Int. Pat. WO 2008065500, 2008.
33. Kawato, H.; Miyazaki, M.; Sugimoto, Y.; Naito, H.; Okayama, T.; Soga, T.; Uoto, K. PCT Int. Pat. WO 2008072655, 2008.
34. Muehlebach, M.; Jeanguenat, A.; Hall, R. G. PCT Int. Pat. WO 2007080131, 2007.
35. Fecht, H. Ber. 1907, 40, 3883-3888
36. Janson, S. E.; Pope, W. J. Proc. R. Soc. 1936, 154, 53-54
37. Wynberg, H.; Houbiers, J. P. M. J. Org. Chem. 1971, 36, 834-842
38. Synthesis of the mono-Boc derivative of 1a was described without characterization in the patent literature; (16) in this work, an analogous approach is used.
39. The preliminary results of this project have been reported previously by our group: Shivanyuk, A. N.; Volochnyuk, D. M.; Komarov, I. V.; Nazarenko, K. G.; Radchenko, D. S.; Kostyuk, A.; Tolmachev, A. A. Chem. Today 2007, 25, 12-13
40. Pigou, P. E.; Schiesser, C. H. J. Org. Chem. 1988, 53, 3841-3843
41. While the work was in progress, an analogous synthesis of compound 7 was reported elsewhere: Kumar, R. J.; Chebib, M.; Hibbs, D. E.; Kim, H.-L.; Salam, N. K.; Hanrahan, J. R.; Johnston, G. A. R. J. Med. Chem. 2008, 51, 3825-3840
42. Radchenko, D. S.; Grygorenko, O. O.; Komarov, I. V. Tetrahedron: Asymmetry 2008, 19, 2924-2930
43. Weatherhead, R. A.; Carducci, M. D.; Mash, E. A. J. Org. Chem. 2009, 74, 8773-8778
44. Wynberg, H.; Houbiers, J. P. M. J. Org. Chem. 1971, 36, 834-842
45. Buchta, E.; Merk, W. Liebigs Ann. 1966, 694, 1-8
46. A slightly different synthesis of 23 has been reported: Jones, B. C. N. M.; Drach, J. C.; Corbett, T. H.; Kessel, D.; Zemlicka, J. J. Org. Chem. 1995, 60, 6277-6280
47. Radchenko, D. S.; Grygorenko, O. O.; Komarov., I. V. Amino Acids 2010, 39, 515-521
48. Wermuth, C.-G.; Langet, T. In 3D QSAR in drug design: theory, methods and applications; Kubiniyi, H., Ed.; ESCOM Science Publishers: Leiden, Holland, 1993; pp 117 - 136.
49. To be more precise, bound unit vectors, see: Tang, K.-T. Mathematical methods for engineers and scientist 2: vector analysis, ordinary differential equations and Laplace transforms; Springer-Verlag: Berlin/Heidelberg, Germany, 2007; pp 3 - 22.
50. In principle, this description can be extended to any conformationally constrained scaffolds possessing two functional groups. It should be noted, however, that due to some flexibility characteristic to any organic molecule (especially to cyclobutane derivatives described in this work), the values of the above-defined geometric parameters can be useful only for semiquantitative considerations. See the Supporting Information for more detailed discussion.
51. See, for example: Fong., C. W.; Grant, H. G. Aust. J. Chem. 1981, 34, 2307-2312
52. Jhon, J. S.; Kang, Y. K. J. Phys. Chem. B 2007, 111, 3496-3507
53. Burkhard, J. A.; Gurot, C.; Knust, H.; Rogers-Evans, M.; Carreira, E. M. Org. Lett. 2010, 12, 1944-1947
54. Zheng, P.-W.; Wang, W.; Duan, X.-M. Acta Crystallogr., Sect. E 2005, 61, o2513
55. Shankland, N.; David, W. I. F.; Shankland, K.; Kennedy, A. R.; Frampton, C. S.; Florence, A. J. Chem. Commun. 2001, 2204-2205
56. Braun, D. E.; Gelbrich, T.; Kahlenberg, V.; Tessadri, R.; Wieser, J.; Griesser, U. J. Cryst. Growth Des. 2009, 9, 1054-1065
57. Peeters, O. M.; Blaton, N. M.; De Ranter, C. J. Acta Crystallogr., Sect. C 1995, 51, 2132-2135
58. Collin, S.; Vercauteren, D. P.; Evrard, G.; Durant, F.; Tollenaere, J. P.; Moereels, H. J. Mol. Struct. 1989, 214, 159-175
59. de Meijere, A.; Williams, C. M.; Kourdioukov, A.; Sviridov, S. V.; Chaplinski, V.; Kordes, M.; Savchenko, A. I.; Stratmann, C.; Noltemeyer, M. Chem.-Eur. J. 2002, 8, 3789-3801
60. Collin, S.; Patiny, A.; Evrard, G.; Durant, F. Bull. Soc. Chim. Belg. 1987, 96, 337-338
61. Collin, S.; Evrard, G.; Durant, F. Acta Crystallogr., Sect. C 1987, C43, 697-699
62. Levina, O. I.; Potekhin, K. A.; Kurkutova, E. N.; Struchkov, Yu. T.; Palyulin, V. A.; Zefirov, N. S. Dokl. Akad. Nauk SSSR 1984, 277, 367
63. The 3-Azaspiro[3.3]heptane scaffold has been recently considered as a possible replacement for piperidine, see: Meyers, M. J.; Muizebelt, I.; van Wiltenburg, J.; Brown, D. L.; Thorarensen, A. Org. Lett. 2009, 11, 3523-3525
64. Burkhard, J. A.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 3524-3527
65. Herzog, H. L. Org. Synth. 1951, 31, 82
66. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, A64, 112-122