Antitumor Benzo Research Articles

Synthesis of derivatives of NK109, 7-OH Benzo[ c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties

The N 5–C 6 double bond of NK109 (an antitumor benzo[ c]phenanthridine alkaloid) is easily reduced under biological environment. To suppress the inactivation caused by reduction, we synthesized 5-, 6-, and 8-substituted NK109. 5-Substituted derivatives ( 4a– c) were reduced more easily than NK109. 6-Substituted ones ( 10a– f) inhibited biological reduction, but showed weak cytotoxic activity. 8 -O-Substituted ones ( 13a– h), especially 8- O-hydroxyethyl NK109 ( 13d), suppressed biological reduction and exhibited strong cytotoxic activity.

Synthesis of some benzo[h]quinoline derivatives

AbstractReaction between 6‐methoxy‐1‐tetralone, methyl propiolate and an ammonia‐saturated methanolic solution led to 5,6‐dihydro‐8‐methoxybenzo[h]quinolin‐2(1H)‐one in good yields. Subsequent aromatization, chlorination, substitution and demethylation enabled us to prepare 2‐amino‐substituted benzo[h]quinoline derivatives. These compounds, which are structurally related to the antitumor benzo[c]phenanthridine alkaloids by deletion of a ring, were tested on cultured murine lymphoblastic leukaemia cells (L1210). Results showed that they are devoid of cytotoxicity.

Chemical transformation of protoberberines. XIII. A novel and efficient synthesis of antitumor benzo[c]phenanthridine alkaloids, nitidine and fagaronine.

An efficient synthesis of nitidine (1a).and fagaronine (1c), antitumor 2, 3, 8, 9-tetraoxygenated benzo [c] phenanthridine alkaloids, has been achieved via regioselective C6-N bond cleavage, followed by consecutive oxy-functionalization and recyclization between the C6 and C13 positions of the starting protoberberines, pseudoberberine (3a) and O-benzyldehydrodiscretine (3b), respectively.

Studies on the chemical constituents of rutaceous plants. LX. Development of a versatile method for syntheses of the antitumor benzo[c]phenanthridine alkaloids. (9). Efficient syntheses and antitumor activities of nitidine and related nonphenolic benzo[c]phenanthridine alkaloids.

Several nonphenolic benzo [c] phenanthridine alkaloids including naturally occurring nitidine (1a) and avicine (1e) were synthesized in excellent yields through an efficient synthetic method developed by us. Antitumor activities of twelve alkaloids including four naturally occurring O5-alkaloids [chelilutine (1g), chelirubine (1h), sanguilutine (1k), and sanguirubine (11)] against Sarcoma 180 were tested. The structure-activity relationship of these alkaloids is discussed.

ChemInform Abstract: STUDIES ON THE CHEMICAL CONSTITUENTS OF RUTACEOUS PLANTS. DEVELOPMENT OF A VERSATILE METHOD FOR SYNTHESIS OF THE ANTITUMOR BENZO(C)PHENANTHRIDINE ALKALOIDS. PART 57. BAEYER‐VILLIGER‐TYPE OXIDATION OF AN IMMONIUM GROUP. THE HE STRUCTURAL ESTABLISHMENT OF NATURALLY OCCURRING AMIDES RELATED TO BENZO(C)PHENANTHRIDINE ALKALOIDS

Chemischer InformationsdienstVolume 15, Issue 48 Natural Products ChemInform Abstract: STUDIES ON THE CHEMICAL CONSTITUENTS OF RUTACEOUS PLANTS. DEVELOPMENT OF A VERSATILE METHOD FOR SYNTHESIS OF THE ANTITUMOR BENZO(C)PHENANTHRIDINE ALKALOIDS. PART 57. BAEYER-VILLIGER-TYPE OXIDATION OF AN IMMONIUM GROUP. THE HE STRUCTURAL ESTABLISHMENT OF NATURALLY OCCURRING AMIDES RELATED TO BENZO(C)PHENANTHRIDINE ALKALOIDS H. ISHII, H. ISHIISearch for more papers by this authorT. ISHIKAWA, T. ISHIKAWASearch for more papers by this authorS.-T. LU, S.-T. LUSearch for more papers by this authorI.-S. CHEN, I.-S. CHENSearch for more papers by this author H. ISHII, H. ISHIISearch for more papers by this authorT. ISHIKAWA, T. ISHIKAWASearch for more papers by this authorS.-T. LU, S.-T. LUSearch for more papers by this authorI.-S. CHEN, I.-S. CHENSearch for more papers by this author First published: November 27, 1984 https://doi.org/10.1002/chin.198448335Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume15, Issue48November 27, 1984 RelatedInformation

Transformation of protoberberines into benzo[ C]phenanthridines a novel and efficient synthesis of antitumor benzo[ C]phenanthridine alkaloids, fagaronine and nitidine

Antileukemic benzo[ C]phenanthridine alkaloids, fagaronine (1a) and nitidine (1c) were synthesized from the corresponding protoberberines through C 6-N bond fission and subsequent cyclization between C 6 and C 13 position of the protoberberines.

A review of the chemistry of the antitumor benzo[c]phenanthridine alkaloids nitidine and fagaronine and of the related antitumor alkaloid coralyne

A review of the chemistry of the antitumor benzo[<i>c</i>]phenanthridine alkaloids nitidine and fagaronine and of the related antitumor alkaloid coralyne

Quino[1,2‐c]quinazolines. I. Synthesis of quino[1,2‐c]quinazolinium derivatives and the related indazolo[2,3‐a]quinoline derivatives as analogs of the antitumor benzo[c]phenanthridine alkaloids

Abstract9,10‐Dimethoxy‐1,2,3,4,12,13‐hexahydro‐1‐oxoquino[1,2‐c]quinazolinium perchlorate, 1,2,3,4,13,24‐hexahydro‐1‐oxo[1,3]dioxolo[4,5‐g]quino[1,2‐c]quinazolinium perchlorate, 6‐methyl‐2,3,9,10‐tetramethoxyquino‐[1,2‐c]quinazolinium perchlorate and 2,3‐dimethoxy‐13‐methyl[1,3]dioxolo[4′,5′:6,7]quino[1,2‐c]quinazolinium perchlorate were synthesized as analogs of the potent antitumor benzo[c]phenanthridine alkaloids nitidine and fagaronine. The related 2,3,8,9‐tetramethoxyindazolo[2,3‐a]quinoline and 2,3‐dimethoxy[1,3]dioxolo‐[4,5‐g]indazolo[2,3‐a]quinoline were also synthesized. Further, the novel formation of 6,7‐dimethoxy‐2‐(2‐ethylamino‐4,5‐dimethoxyphenyl)quinoline via reductive alkylation with Raney nickel in refluxing ethanol is also reported.

Improvement of the Synthetic Method of Anti-tumor Benzo[c]phenanthridine Alkaloids

Improvement of the Synthetic Method of Anti-tumor Benzo[c]phenanthridine Alkaloids