Dependence of reactivity of a novel 2,6-diamino pyridine-based enediyne on the extent of salt formation with external acids: a possible implication in pH based drug design

被引：8

作者：

Basak, A ^{[1
]}

Kar, M ^{[1
]}

Mandal, S ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 08期

关键词：

enediyne; Bergman cyclization; calorimetry; drug; design;

D O I：

10.1016/j.bmcl.2005.02.051

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel pyridine diamine-based cyclic enediyne 1 was synthesized by bis-N-alkylation of 2,6-bis-sulfonamido pyridine 6 followed by deprotection with thiophenol. A variety of salts la-c of the parent amine 1 were prepared. Thermal reactivity studies indicated a dependence of the reactivity upon the extent of salt formation. This observation may be useful in pH-based design of enediynes. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2061 / 2064

页数：4

共 36 条

[1] Benzene fused monocyclic enediynyl amides: Synthesis, reactivity and DNA-cleavage activity in comparison to the corresponding sulfonamides [J].

Basak, A ;

Mandal, S ;

Das, AK ;

Bertolasi, V .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (06) :873-877

[2] ENZYMATIC-HYDROLYSIS OF (+/-)-TRANS-1,2-DIACETOXYCYCLOALKANES - A FACILE ROUTE TO OPTICALLY-ACTIVE CYCLOALKANE-1,2-DIOLS [J].

CROUT, DHG ;

GAUDET, VSB ;

LAUMEN, K ;

SCHNEIDER, MP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :808-810

[3] Synthesis and thermal rearrangement of C,N-dialkynyl imines: A potential Aza-Bergman route to 2,5-didehydropyridine [J].

David, WM ;

Kerwin, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) :1464-1465

[4] CHARACTERIZATION OF THE INVITRO CYCLIZATION CHEMISTRY OF CALICHEAMICIN AND ITS RELATION TO DNA CLEAVAGE [J].

DEVOSS, JJ ;

HANGELAND, JJ ;

TOWNSEND, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4554-4556

[5] SITE-SPECIFIC ATOM TRANSFER FROM DNA TO A BOUND LIGAND DEFINES THE GEOMETRY OF A DNA CALICHEAMICIN GAMMA-1I COMPLEX [J].

DEVOSS, JJ ;

TOWNSEND, CA ;

DING, WD ;

MORTON, GO ;

ELLESTAD, GA ;

ZEIN, N ;

TABOR, AB ;

SCHREIBER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9669-9670

[6] 2,4-dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines. [J].

Fukuyama, T ;

Cheung, M ;

Jow, CK ;

Hidai, Y ;

Kan, T .

TETRAHEDRON LETTERS, 1997, 38 (33) :5831-5834

[7] ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .3. STRUCTURES OF ESPERAMICINS-A1, ESPERAMICIN-A2, AND ESPERAMICIN-A1B [J].

GOLIK, J ;

DUBAY, G ;

GROENEWOLD, G ;

KAWAGUCHI, H ;

KONISHI, M ;

KRISHNAN, B ;

OHKUMA, H ;

SAITOH, K ;

DOYLE, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3462-3464

[8] The chemistry of enediynes, enyne allenes and related compounds [J].

Grissom, JW ;

Gunawardena, GU ;

Klingberg, D ;

Huang, DH .

TETRAHEDRON, 1996, 52 (19) :6453-6518

[9] Chemistry of the 2,5-didehydropyridine biradical: Computational, kinetic, and trapping studies toward drug design [J].

Hoffner, J ;

Schottelius, MJ ;

Feichtinger, D ;

Chen, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :376-385

[10]

KONIG B, 1994, J ORG CHEM, V59, P7142

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