Ring-expansion synthesis and crystal structure of dimethyl 4-ethyl-1,4,5,6,7,8-hexa-hydro-azonino[5,6-b]indole-2,3-di-carboxyl-ate.
The title compound, C20H24N2O4, is the product of a ring-expansion reaction from a seven-membered hexa-hydro-azepine to a nine-membered azonine. The azonine ring of the mol-ecule adopts a chair-boat conformation. In the crystal, mol-ecules are linked by bifurcated N-H⋯(O,O) hydrogen bonds, generating [010] zigzag chains. The title compound shows inhibitory activity against acetyl-cholinesterase and butyrylcholinesterase, and might be considered as a candidate for the design of new types of anti-Alzheimer's drugs.
Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi, Vietnam; Graduate University of Science and Technology, 18 Hoang Quoc Viet, Hanoi, Vietnam.
Van Tuyen
VT
Nguyen
Organic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation.
Elena A
EA
Sorokina
Organic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation.
Anna V
AV
Listratova
Organic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation.
Leonid G
LG
Voskressensky
Inorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation.
Nikolai N
NN
Lobanov
National Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation.
Pavel V
PV
Dorovatovskii
National Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation.
Yan V
https://orcid.org/0000-0003-2266-8944
YV
Zubavichus
Inorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow 117198, Russian Federation; X-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., B-334, Moscow 119991, Russian Federation.
Victor N
https://orcid.org/0000-0001-8806-2975
VN
Khrustalev
Alz­heim­er’s disease; azonino­indoles; crystal structure; natural alkaloids; synchrotron radiation