Abstract
Reactions of pyrazolo[3,4-d]pyrimidine-containing hydrazines with pregnenolone derivatives were studied. The reaction of 16α,17α-epoxy-3β-hydroxy-5-pregnen-20-one and its 3-O-acetyl derivative with 6-hydrazino-3,4-dimethyl-1H-pyrazolo[3,4-d]pyrimidine and 4-hydrazino-3-methyl-6-phenyl-1H-pyrazolo[3,4-d]pyrimidine afforded new androsteno[17,16-d]pyrazoles with pyrazolo[3,4-d]pyrimidine fragments. The reaction of 3β-hydroxypregna-5,16-dien-20-one and its 3-O-acetyl derivative with 4-hydrazino-3-methyl-6-phenyl-1H-pyrazolo[3,4-d]pyrimidine gave hydrazones at position 20 of the pregnenolone molecule, which upon melting undergo cyclization to androsteno[17,16-d]-2′-pyrazolines. Reflux of the hydrazone in mesitylene in the presence of MCPBA leads to a mixture of three products, namely, androsteno[17,16-d]-2′-pyrazoline, androsteno[17,16-d]pyrazole, and dodecahydro-13H-phenanthro[1′,2′:5,6]pyrano[2,3-d]pyrazole derivative resulting from the oxidative expansion of the steroid cyclopentane ring D.
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References
S. V. Stulov, A. Yu. Misharin, Chem. Heterocycl. Compd., 2012, 48: 1431.
P. Traxler, G. Bold, J. Frei, M. Lang, N. Lydon, H. Mett, E. Buchdunger, T. Meyer, M. Mueller, P. Furet, J. Med. Chem., 1997, 40: 3601.
S. Schenon, S. Zanoli, C. Brullo, E. Crespan, G. Maga, Curr. Drug. Ther., 2008, 3: 158.
S. Schenon, O. Bruno, M. Radi, M. Botta, Mini-Rev. Org. Chem., 2009, 6: 220.
K. J. Curran, J. C. Verheij en, J. Kaplan, D. J. Richard, L. Toral-Barza, I. Hollander, J. Lucas, S. Ayral-Kaloustian, K. Yu, A. Zask, Bioorg. Med. Chem. Lett., 2010, 20: 1440.
Int. Appl. WO 2009/097446 A1; Chem. Abstrs, 2009, 151: 221198.
H. A. Burch, J. Med. Chem., 1968, 11: 79.
J. L. Avila, M. A. Polegre, A. R. Avila, K. Robins, Comp. Biochem. Physiol., 1986, 83C, 285.
G. A. Bhat, J. G. Montero, R. P. Panzica, L. L. Worting, L. B. Towsend, J. Med. Chem., 1981, 24: 1165.
A. V. Kamernitskii, N. S. Pavlova-Grishina, A. V. Skorova, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1980, 29: 843.
J.-B. Cazaux, R. Jacquier, G. Maury, Tetrahedron Lett., 1971, 1: 41.
B. Green, B. L. Jensen, P. L. Lalan, Tetrahedron, 1978, 34: 1633.
M. I. Merlani, E. R. Kamertelidze, K. Papadopolus, N. I. Men’shova, Russ. J. Bioorg. Chem., 2004, 30: 552.
S. Ahmed, R. C. Boruah, M. Longchar, Indian J. Chem., 1999, 38B, 125.
I. V. Zavarzin, A. V. Kamernitsky, V. V. Chertkova, E. I. Chernoburova, V. N. Yarovenko, M. M. Krayushkin, V. V. Kachala, ARKIVOC, 2008, IV, 62.
I. V. Zavarzin, V. V. Chertkova, I. S. Levina, E. I. Chernoburova, Russ. Chem. Rev., 2011, 80: 693.
G. Visbal, G. San-Blas, A. Maldonado, A. Alvarez-Aular, M. V. Capparelli, J. Murgich, Steroids, 2011, 76: 1069.
A. V. Komkov, I. V. Zavarzin, A. S. Shashkov, Russ. Chem. Bull., 2014, 63: 462.
A. V. Komkov, A. S. Shashkov, S. V. Baranin, V. A. Dorokhov, Russ. Chem. Bull., 2013, 62: 1248.
P. L. Julian, E. W. Meyer, W. J. Karpel, I. R. Waller, J. Am. Chem. Soc., 1950, 72: 5145.
A. A. Akhrem, V. A. Dubrovskii, A. V. Kamernitskii, A. V. Skorova, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1968, 17: 2657.
A. A. Akhrem, A. V. Kamernitskii, A. V. Skorova, N. S. Pavlova-Grishina, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1973, 22: 869.
V. A. Dorokhov, M. F. Gordeev, E. M. Shashkova, A. V. Komkov, V. S. Bogdanov, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1991, 40: 2274.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1088–1099, June, 2018.
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Komkov, A.V., Chizhov, A.O., Shashkov, A.S. et al. Synthesis of androsteno[17,16-d]pyrazoles and androsteno[17,16-d]-2′-pyrazolines with pyrazolo[3,4-d]pyrimidine fragments. Russ Chem Bull 67, 1088–1099 (2018). https://doi.org/10.1007/s11172-018-2185-5
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DOI: https://doi.org/10.1007/s11172-018-2185-5