481-87-8Relevant academic research and scientific papers
IBOGAINE ANALOGS AS THERAPEUTICS FOR NEUROLOGICAL AND PSYCHIATRIC DISORDERS
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Page/Page column 67, (2022/02/05)
The present invention provides a compound having the structure: formula wherein X1 is H or alkyl; Y1 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -cycloalkyl, - aryl, heteroaryl, -alkyl-Y3 or -alkyl-C(O)Y4, and Y2 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -cycloalkyl, - aryl, heteroaryl, -alkyl-Yg or -alkyl-C(O)Y4, wherein each Y3 is, independently, -OH, -O(alkyl), -NH2, - NH(alkyl) or halogen, and each Y4 is, independently, -OH, -O(alkyl), -NH2, -NH(alkyl) or -N(alkyl)2; Z1 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -aryl, heteroaryl, -alkyl-Zg or -alkyl-C(O)Z4, and Z2 is H, -alkyl, -alkenyl, -alkynyl, alkylaryl, -aryl, heteroaryl, -alkyl-Zg or -alkyl-C(O)Z4, wherein each Z3 is, independently, -OH, -O(alkyl), -NH2, - NH(alkyl) or halogen, and each Z4 is, independently, -OH, -O(alkyl), -NH2, -NH(alkyl) or -N(alkyl)2; R1, R2, R3 and R4 are each, independently, -H, -F, -Cl, -Br, -I, -NO2, -CN, -CF3, -CF2H, -OCF3, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), -OH, -OAc, -O-(alkyl), -O-(alkenyl), - O-(alkynyl), -O-(aryl), -O-(heteroaryl), -SH, -S-(alkyl), S (alkenyl), -S-(alkynyl), -S-(aryl), -S-(heteroaryl), -NH2, -NH- (alkyl), -NH-(alkenyl), -NH-(alkynyl), -NH-(aryl), -NH- (heteroaryl), -C(0)R5, -S(O)R5, -SO2R5, -NHSO2R5, -0C(0)R5, SC(0)R5, -NHC(O)R6 or -NHC(S)R6, wherein each R5 is, independently, -(alkyl), -(aryl), (heteroaryl), -OH, -O(alkyl), -NH2, -NH(alkyl) or N(alkyl)2, and wherein each R6 is, independently, -(alkyl), -(aryl), -O- (alkyl), -S-(alkyl), -S-(aryl), -NH2, -NH(alkyl) or N(alkyl)2, wherein the compound is other than any of ibogaine, ibogamine, N- methyl-ibogaine, N-methyl-noribogaine, N-ethyl-noribogaine, N-methyl- ibogamine or 10-ethoxy-ibogamine, or a pharmaceutically acceptable salt of the compound, and methods of using the composition to treat pain, depressive disorders, mood disorders, anxiety disorders, substance use disorders, opioid use disorders, and opioid withdrawal symptoms.
Reductive Heck coupling: An efficient approach toward the iboga alkaloids. Synthesis of ibogamine, epiibogamine and iboga analogs
Jana, Goutam Kumar,Sinha, Surajit
, p. 1671 - 1674 (2012/04/11)
A mild and efficient synthetic route to the iboga scaffold by employing reductive-Heck type annulation is described. The utility of this process is demonstrated by the direct access to the ibogamine, epiibogamine and iboga-analogs. The cyclization precursors were readily obtained from 2-iodoaniline by heteroannulation reaction with suitable alkynes followed by iodination.
Catalyzed asymmetric Diels - Alder reactions of benzoquinone. Total synthesis of (-)-ibogamine
White, James D.,Choi, Younggi
, p. 4306 - 4327 (2007/10/03)
The Diels - Alder reaction of 1,4-benzoquinone with 1,3-dienes catalyzed by Mikami's [Ti{(S)-binol(2 -)}Cl2] complex (binol = [1,1′-binaphthalene]-2,2′-diol) gives cycloadducts in good yield and in high enantiomer excess. A model is proposed to
Catalyzed asymmetric Diels-Alder reaction of benzoquinone. Total synthesis of (-)-ibogamine
White, James D.,Choi, Younggi
, p. 2373 - 2376 (2007/10/03)
(equation presented) The Diels-Alder addition of diene 2 with benzoquinone catalyzed by (S)-BINOL-TiCl2 produced cycloadduct 5 in >65% yield and 87% ee. The cycloadduct was transformed into (-)-ibogamine in nine steps (10% overall yield from be
A novel approach to iboga alkaloids: Total synthesis of (±)-ibogamine and (±)-epi-ibogamine
Henry Jr., Kenneth J.,Grieco, Paul A.,DuBay, William J.
, p. 8289 - 8292 (2007/10/03)
A novel approach to the total synthesis of (±)-ibogamine and (±)-epi-ibogamine, featuring electrophilic substitution at C(2) of N'-CBZ-tryptamine by an allylic acetate, is described.
1,6-dihydro-3(2H)-pyridinones. X. 2-azabicyclooctane Ring Formation via Intramolecular Michael reaction: Total synthesis of (+/-)-Ibogamine and (+/-)-Epiibogamine
Imanishi, Takeshi,Yagi, Noriyuki,Hanaoka, Miyoji
, p. 4202 - 4211 (2007/10/02)
A new elaboration method for the 2-azabicyclooctane ring via an intramolecular Michael reaction has been developed and applied to the total synthesis of (+/-)-ibogamine (1) and (+/-)-epiibogamine (2).The unsaturated estert (9) derived from ethyl 1,
Alkaloid studies. 8. Isolation and characterization of alkaloids of Tabernaemontana heyneana Wall and antifertility properties of coronaridine.
Meyer,Coppola,Goldman
, p. 1199 - 1201 (2007/10/09)
In this study, the roots of Tabernaemontana heyneana Wall were examined and the isolation and identification of additional indole alkaloids and some pharmacological properties of coronaridine are described. Extraction of the roots yielded the alkaloids coronaridine, voacangine, ibogamine, 19-oxocoronaridine, and the pseudoindoxyl of voacangine. An acqueous ethanolic extract of the roots was found to prevent fertilization of adult female rats when administered orally. After the residue of this extract was treated chromatographic fractionation on silica gel yielded the alkaloid coronaridine. When administered to adult female rats, orally, coronaridine hydrochloride at levels of 5 mg/kg/day or above prevented pregnancy. Voacangine, assayed by the same procedure, did not prevent pregnancies. Data indicated that coronaridine was weakly estrogenic.
