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Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity

Ol'ga Nikolaevna Zefirova ^{1, 2}

Ol'ga Nikolaevna Zefirova

Evgeniya Denisovna Plotnikova ¹

Evgeniya Denisovna Plotnikova

Evgeniya Vladimirovna Nurieva ¹

Evgeniya Vladimirovna Nurieva

Danil I Peregud ³

Danil I Peregud

Mikhail Valeryevich Onufriev ⁴

Mikhail Valeryevich Onufriev

Natalia Valer'evna Gulyaeva ⁴

Natalia Valer'evna Gulyaeva

¹ Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation

² Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

³ National Research Center on Addictions, Ministry of Health and Social Development of the Russian Federation, Moscow, Russian Federation

⁴ Institute for Higher Nervous Activity and Neurophysiology, Russian Academy of Sciences, Moscow, Russian Federation

10.1016/j.mencom.2013.03.006

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Published 2013-03-06

Communication , Volume 23, Issue 2, 76-77

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Zefirova O. N. et al. Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity // Mendeleev Communications. 2013. Vol. 23. No. 2. pp. 76-77.

GOST all authors (up to 50) Copy

Zefirova O. N., Plotnikova E. D., Nurieva E. V., Peregud D. I., Onufriev M. V., Gulyaeva N. V. Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity // Mendeleev Communications. 2013. Vol. 23. No. 2. pp. 76-77.

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TY - JOUR

DO - 10.1016/j.mencom.2013.03.006

UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.03.006

TI - Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity

T2 - Mendeleev Communications

AU - Zefirova, Ol'ga Nikolaevna

AU - Plotnikova, Evgeniya Denisovna

AU - Nurieva, Evgeniya Vladimirovna

AU - Peregud, Danil I

AU - Onufriev, Mikhail Valeryevich

AU - Gulyaeva, Natalia Valer'evna

PY - 2013

DA - 2013/03/06

PB - Mendeleev Communications

SP - 76-77

IS - 2

VL - 23

ER -

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@article{2013_Zefirova,

author = {Ol'ga Nikolaevna Zefirova and Evgeniya Denisovna Plotnikova and Evgeniya Vladimirovna Nurieva and Danil I Peregud and Mikhail Valeryevich Onufriev and Natalia Valer'evna Gulyaeva},

title = {Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity},

journal = {Mendeleev Communications},

year = {2013},

volume = {23},

publisher = {Mendeleev Communications},

month = {Mar},

url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.03.006},

number = {2},

pages = {76--77},

doi = {10.1016/j.mencom.2013.03.006}

}

MLA

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Zefirova, Ol'ga Nikolaevna, et al. “Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity.” Mendeleev Communications, vol. 23, no. 2, Mar. 2013, pp. 76-77. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.03.006.

Abstract

2-Thia-4-azabicyclo[3.3.1]non-3-en-3-amine was synthesized as a lipophilic analogue of NO-synthase inhibitor 2-amino-5,6-dihydro- 4H-1,3-thiazine and found to be a potent inhibitor of inducible NO-synthase in vitro. The crystal structure of the key intermediate 2-thia-4-azabicyclo[3.3.1]nonane-3-thione (obtained by cyclization of trans-3-bromocyclohexylamine with carbon disulfide) was determined by X-ray analysis.

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