Synthesis and Antitumor Activity of Fused Quinoline Derivatives. III. Novel N-Glycosylaminoindolo(3,2-b)quinolines.

Takeuchi, Yasuo; Chang, M.R.; Hashigaki, Kuniko; Tashiro, Tazuko; Tsuruo, Takashi; Tsukagoshi, Shigeru; Yamato, Masatoshi

doi:10.1248/cpb.40.1481

Cited by 8 publications

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“…Due to their significance, numerous synthetic approaches have been developed for the construction of such structural motifs. These approaches could be categorized simply into three strategies on the basis of the ring-constructing method ( Figure 1 ), which are the heteroaryl ring formation (strategy a) [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ], the central pyridyl ring formation (strategy b) [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ], and the formation of both rings (strategy c) [ 4 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 ]. Although there are advantages and disadvantages to each strategy from various aspects, the strategy b seems to be the most user-friendly in terms of the accessibility of the starting substrates.…”

Section: Introductionmentioning

confidence: 99%

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

et al. 2018

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We disclose herein the first synthetic method that is capable of offering heteroaryl[b]quinolines (HA[b]Qs) with structural diversity, which include tricyclic and tetracyclic structures with (benzo)thienyl, (benzo)furanyl, and indolyl rings. The target HA[b]Q is addressed by the annulation of o-acylanilines and MeO–heteroarenes with the aid of an indium Lewis acid that effectively works to make two different types of the N–C and C–C bonds in one batch. A series of indolo[3,2-b]quinolines prepared here can be subsequently transformed to structurally unprecedented cryptolepine derivatives. Mechanistic studies showed that the N–C bond formation is followed by the C–C bond formation. The indium-catalyzed annulation reaction thus starts with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion, and thereby the N–C bond is formed. The resulting intermediate then cyclizes to make the C–C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, providing the HA[b]Q after aromatizing dehydration.

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Section: Introductionmentioning

confidence: 99%

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

et al. 2018

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“…Recently, the discovery of many potent clinically important antitumor drugs having a quinoline moiety has been reported . Also, a large number of quinoline derivatives are involved in the manufacture of a wide variety of medicinals and pharmaceuticals, including antibiotic, antimalarial, antibacterial, antimicrobial, and analgesic drugs.…”

Section: Introductionmentioning

confidence: 99%

Electrolytic Partial Fluorination of Organic Compounds. 31.¹ Regioselective Anodic Fluorination of 2-Quinolyl and 4-(7-Trifluoromethyl)quinolyl Sulfides and the Factors Affecting Its Optimization

Dawood

1998

J. Org. Chem.

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Electrochemical fluorination of 2-quinolyl and 4-(7-trifluoromethyl)quinolyl sulfides bearing an electron-withdrawing group at the position alpha to the sulfur atom was studied. Fluorination was successfully carried out using Et(4)NF.nHF (n = 3, 4) and Et(3)N.3HF as a supporting electrolyte and a fluoride ion source in dimethoxyethane in a divided cell to provide the corresponding alpha-fluorinated sulfides in good yields. A trifluoromethyl group positioned on the quinoline ring significantly enhanced anodic alpha-fluorination. 4-(Methylthio)-7-(trifluoromethyl)quinoline was also found to undergo anodic fluorination efficiently. Solvent effects of various donor numbers were also established.

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ChemInform Abstract: Synthesis and Antitumor Activity of Fused Quinoline Derivatives. Part 3. Novel N‐Glycosylaminoindolo(3,2‐b)quinolines.

Takeuchi¹,

Chang²,

Hashigaki³

et al. 1993

ChemInform

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Synthesis and Antitumor Activity of Fused Quinoline Derivatives. Part 3. Novel N-Glycosylaminoindolo(3,2-b)quinolines.-The synthesis of 10H-indolo(3,2-b)quinolines such as (II), (V), (VII), (IX), and (XI) possessing a nitro, amino, acetamido, methanosulfonamido, or glycosylamino group is described. The influence of the different functional groups on the antitumor activity is tested. -(TAKEUCHI, Y.; CHANG, M.-R.; HASHIGAKI, K.; TASHIRO, T.; TSURUO, T.; TSUKAGOSHI, S.; YAMATO, M.; Chem.

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Synthesis and Antitumor Activity of Fused Quinoline Derivatives. III. Novel N-Glycosylaminoindolo(3,2-b)quinolines.

Cited by 8 publications

References 0 publications

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

Electrolytic Partial Fluorination of Organic Compounds. 31.¹ Regioselective Anodic Fluorination of 2-Quinolyl and 4-(7-Trifluoromethyl)quinolyl Sulfides and the Factors Affecting Its Optimization

ChemInform Abstract: Synthesis and Antitumor Activity of Fused Quinoline Derivatives. Part 3. Novel N‐Glycosylaminoindolo(3,2‐b)quinolines.

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Synthesis and Antitumor Activity of Fused Quinoline Derivatives. III. Novel N-Glycosylaminoindolo(3,2-b)quinolines.

Cited by 8 publications

References 0 publications

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

Electrolytic Partial Fluorination of Organic Compounds. 31.1 Regioselective Anodic Fluorination of 2-Quinolyl and 4-(7-Trifluoromethyl)quinolyl Sulfides and the Factors Affecting Its Optimization

ChemInform Abstract: Synthesis and Antitumor Activity of Fused Quinoline Derivatives. Part 3. Novel N‐Glycosylaminoindolo(3,2‐b)quinolines.

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Electrolytic Partial Fluorination of Organic Compounds. 31.¹ Regioselective Anodic Fluorination of 2-Quinolyl and 4-(7-Trifluoromethyl)quinolyl Sulfides and the Factors Affecting Its Optimization