Synthesis of new A-conjugated Quinolone and Spiroindole Dammaranes by the Ozonolysis of 2,3-Indolodipterocarpol

Смирнова, И. Е.; Khusnutdinova, É. F.; Лобов, А. Н.; Казакова, О. Б.

doi:10.1177/1934578x1801300516

Cited by 3 publications

(3 citation statements)

References 25 publications

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“…The main product of this reaction is compound 219 with a [b]annulated polycarbocyclic fragment to 4-quinolone (73 %), along with which minor spiro-fused indoles 220a and 220b were also obtained (Scheme 57). [245] It was previously shown that the interaction of Naryl or N-alkyl sulfonates of 3-(indol-3-yl)propylamines with PIDA (phenyliodine(III) diacetate) leads to cyclization to form a spiro-fused indolenine-pyrrolidine backbone. [246] Later this approach was distributed to 2-(indol-3-ylmethyl)anilines 221 (Y=CH 2 ) and 2-(indol-3-ylthio) analog of arylsulfonates (Y=S, only one example, 64 % yield).…”

Section: The Indole Dearomatization Strategy In the Synthesis Of Spirmentioning

confidence: 99%

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Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

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Section: The Indole Dearomatization Strategy In the Synthesis Of Spirmentioning

confidence: 99%

“…The main product of this reaction is compound 219 with a [ b ]‐annulated polycarbocyclic fragment to 4‐quinolone (73 %), along with which minor spiro‐fused indoles 220a and 220b were also obtained ( Scheme 57). [245] …”

Section: Syntheses Of Spiroheterocycles From 3‐alkylidene‐indol‐2‐onementioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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“…For example, oxidation of an aromatic moiety by H 2 O 2 provides the ursane indoloquinone formation with anticancer properties (Hao et al., 2016). The oxidative rearrangement of platanic acid and 28‐oxo‐allobetulone indoles to spiro‐oxindoles and cleavage to quinolones using dimethyldioxorane and ozone as oxidants was successfully developed and led to the antiviral agents (Khusnutdinova et al., 2019; Smirnova, Khusnutdinova, Lobov & Kazakova, 2018). The first example of N ‐propargylation of indolo‐triterpenoids (from abeo ‐lupane and 28‐oxo‐allobetulone) and their following modification using a Cu(I)‐catalyzed Mannich reaction was demonstrated (Khusnutdinova, Petrova, Bashirova, & Kazakova, 2019).…”

Section: Introductionmentioning

confidence: 99%

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

Petrova,

Tretyakova,

Khusnutdinova

et al. 2023

Chem Biol Drug Des

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Oleanolic and glycyrrhetic acids alkyne derivatives were synthesized as a result of propargylation of the indole NH‐group condensed with the triterpene A‐ring, the following aminomethylation led to a series of Mannich bases. The synthesized compounds were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in Madin‐Darby canine kidney (MDCK) cell culture and SARS‐CoV‐2 pseudovirus in baby hamster kidney‐21‐human angiotensin‐converting enzyme 2 (BHK‐21‐hACE2) cells. Mannich bases of oleanolic and glycyrrhetic acids N‐propargylated indoles 7, 8, and 12 were the most efficacious against influenza virus A with IC50 7–10 μM together with a low toxicity (CC50 > 145 μM) and high selectivity index SI value 20. Indolo‐oleanolic acid morpholine amide Mannich base holding N‐methylpiperazine moiety 9 showed anti‐SARS‐CoV‐2 pseudovirus activity with EC50 value of 14.8 μM. Molecular docking and dynamics modeling investigated the binding mode of the compounds 7 and 12 into the binding pocket of influenza A virus M2 protein and compound 9 into the RBD domain of SARS‐CoV‐2 spike glycoprotein.

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Asymmetric Intramolecular Amination Catalyzed with Cp*Ir-SPDO via Nitrene Transfer for Synthesis of Spiro-Quaternary Indolinone

Wei,

Li,

Wang

et al. 2024

J. Am. Chem. Soc.

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An asymmetric intramolecular spiro-amination to high steric hindering α-C−H bond of 1,3-dicarbonyl via nitrene transfer using inactive aryl azides has been carried out by developing a novel Cp*Ir(III)-SPDO (spiro-pyrrolidine oxazoline) catalyst, thereby enabling the first successful construction of structurally rigid spiro-quaternary indolinone cores with moderate to high yields and excellent enantioselectivities. DFT computations support the presence of double bridging H−F bonds between [SbF 6 ] − and both the ligand and substrate, which favors the plane-differentiation of the enol π-bond for nitrenoid attacking. These findings open up numerous opportunities for the development of new asymmetric nitrene transfer systems.

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Synthesis of new A-conjugated Quinolone and Spiroindole Dammaranes by the Ozonolysis of 2,3-Indolodipterocarpol

Cited by 3 publications

References 25 publications

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

Asymmetric Intramolecular Amination Catalyzed with Cp*Ir-SPDO via Nitrene Transfer for Synthesis of Spiro-Quaternary Indolinone

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