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Indole compound with optical activity as well as synthesis method and application thereof

An indole compound and optically active technology, which is applied in the field of optically active indole compounds, can solve the problem of ineffective synthesis of cyano-containing quaternary carbon chiral centers, and achieve good anti-hepatitis B virus activity

Active Publication Date: 2021-06-15
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there is no efficient method for the synthesis of indoles containing cyanoquaternary carbon chiral centers

Method used

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  • Indole compound with optical activity as well as synthesis method and application thereof
  • Indole compound with optical activity as well as synthesis method and application thereof
  • Indole compound with optical activity as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]Embodiment 1: With N-(2-(5,5-dicyano-6-phenylhexane-1-yne-alkyl)phenyl)-4-methylbenzenesulfonamide as standard substrate, for Study on reaction solvents of palladium-catalyzed synthesis of indoles with cyano-chiral quaternary carbon centers at the β-position:

[0038]

[0039]

[0040] Wherein mol% refers to the relative molar weight, equiv represents the equivalent, the yield is the NMR yield, and the brackets are the separation yield. The amount of ligand in condition 10 is 12mol%, and the amount of ligand in condition 11 is 5mol%. Phase determination, condition 5 or condition 10 is the best reaction condition.

Embodiment 2

[0041] Embodiment 2: With N-(2-(5,5-dicyano-6-phenylhexane-1-yne-alkyl)phenyl)-4-methylbenzenesulfonamide as standard substrate, for Palladium-catalyzed reaction catalyst precursors for the synthesis of indoles containing cyano-chiral quaternary carbon centers at the β-position:

[0042]

[0043]

[0044]

[0045] Among them, mol% refers to the relative molar weight, equiv represents the equivalent, and the yield is the nuclear magnetic yield. Condition 7 adds 20mol% AgSbF 6 , Condition 1 is the best reaction condition, er is determined by high performance liquid chromatography.

Embodiment 3

[0046] Example 3: With N-(2-(5,5-dicyano-6-phenylhexane-1-yne-alkyl)phenyl)-4-methylbenzenesulfonamide as standard substrate, for Palladium-catalyzed reaction ligands for the synthesis of indoles with cyano-containing chiral quaternary carbon centers at the β-position:

[0047]

[0048]

[0049]

[0050]

[0051] Wherein mol% refers to relative molar weight, equiv represents equivalent, yield is NMR yield, er is determined by high performance liquid phase, and condition 2 is the best reaction condition.

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Abstract

The invention discloses an indole compound with optical activity as well as a synthesis method and application thereof. The indole compound is an indole compound containing a cyano quaternary carbon chiral center, and the synthesis method of the indole compound is a palladium-catalyzed alkynylamine palladium asymmetric cyano addition reaction. The compound has an obvious inhibition effect on hepatitis B virus (HBV), and is a potential novel compound for preparing drugs for treating HBV.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an optically active indole compound, a synthesis method and an application thereof. Background technique [0002] Indole is an important skeleton of many alkaloids and drug molecules with important biological significance and rich stereochemical structures [(a) M.Usman, X.-D.Hu, W.-B.Liu, Chin.J.Chem .2020, 38, 737; (b) R. Littell, E.N. Greenblatt, G.R. Allen, J. Med. Chem. 1972, 15, 875; (c) T.S. Kam, G. Subramaniam, W. Chen, Phytochemistry 1999, 51, 159; (d) T .Zeng, X.-Y.Wu, S.-X.Yang, W.-C.Lai, S.-D.Shi, Q.Zou, Y.Liu, L.-M.Li, J.Nat. Prod.2017,80,864; (e) W.-S.Yap, C.-Y.Gan, K.-S.Sim, S.-H.Lim, Y.-Y.Low, T.-S.Kam , J. Nat. Prod. 2016, 79, 230.]. So far, using indole as a key intermediate, the total synthesis of more than ten kinds of Aspidosperma and Kopsia family alkaloids has been realized, and these methods all use the all-carbon quaternary carbon center at th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88C07D409/06C07D405/06C07D209/94C07D209/56C07D471/20C07D471/04C07D498/20C07D491/052C07D495/04C07D491/044C07D487/04A61P31/20
CPCC07D209/88C07D409/06C07D405/06C07D209/94C07D209/56C07D471/20C07D471/04C07D498/20C07D491/052C07D495/04C07D491/044C07D487/04A61P31/20C07B2200/07
Inventor 刘文博胡旭东夏宇尘华容
Owner WUHAN UNIV
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