PH DEPENDENT CYCLOAROMATIZATION OF ENEDIYNE MODEL COMPOUNDS VIA ENYNE-ALLENE INTERMEDIATES

被引：22

作者：

NAOE, Y ^{[1
]}

KIKUISHI, J ^{[1
]}

ISHIGAKI, K ^{[1
]}

IITSUKA, H ^{[1
]}

NEMOTO, H ^{[1
]}

SHIBUYA, M ^{[1
]}

机构：

[1] UNIV TOKUSHIMA,FAC PHARMACEUT SCI,TOKUSHIMA 770,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 50期

关键词：

D O I：

10.1016/0040-4039(95)01974-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cis-enediyne derivatives 1 underwent Myers-type cycloaromatization under acidic conditions via the enyne-allene intermediate 2 by the triggering action of the hydroxy group. Compound 1 showed pH dependent DNA-cleaving activity.

引用

页码：9165 / 9168

页数：4

共 11 条

[1] STEREOSELECTIVE SYNTHESIS OF BOTH (E)-1,2,4-HEPTATRIEN-6-YNES AND (Z)-1,2,4-HEPTATRIEN-6-YNES - FORMATION OF AN ALPHA,3-DEHYDROTOLUENE BIRADICAL, TRAPPING BY AN INTRAMOLECULAR CARBON CARBON DOUBLE-BOND, AND DECAY OF THE RESULTING NEW BIRADICAL VIA AN INTRAMOLECULAR ROUTE
ANDEMICHAEL, YW
GU, YG
WANG, KK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) : 794 - 796
[2] DESIGN AND DYNAMICS OF A CHEMICALLY TRIGGERED REACTION CASCADE LEADING TO BIRADICAL FORMATION AT SUBAMBIENT TEMPERATURE
MYERS, AG
DRAGOVICH, PS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (25) : 9130 - 9132
[3] THERMAL GENERATION OF ALPHA,3-DEHYDROTOLUENE FROM (Z)-1,2,4-HEPTATRIEN-6-YNE
MYERS, AG
KUO, EY
FINNEY, NS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 8057 - 8059
[4] BIRADICAL FORMATION FROM ACYCLIC CONJUGATED ENEYNE-ALLENE SYSTEM RELATED TO NEOCARZINOSTATIN AND ESPERAMICIN-CALICHEMICIN
NAGATA, R
YAMANAKA, H
OKAZAKI, E
SAITO, I
[J]. TETRAHEDRON LETTERS, 1989, 30 (37) : 4995 - 4998
[5] DNA CLEAVAGE BY ACYCLIC ENEYNE-ALLENE SYSTEMS RELATED TO NEOCARZINOSTATIN AND ESPERAMICIN-CALICHEAMICIN
NAGATA, R
YAMANAKA, H
MURAHASHI, E
SAITO, I
[J]. TETRAHEDRON LETTERS, 1990, 31 (20) : 2907 - 2910
[6] DNA CLEAVAGE AND ANTITUMOR-ACTIVITY OF DESIGNED MOLECULES WITH CONJUGATED PHOSPHINE OXIDE-ALLENE-ENE-YNE FUNCTIONALITIES
NICOLAOU, KC
MALIGRES, P
SHIN, J
DELEON, E
RIDEOUT, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) : 7825 - 7826
[7] SWITCHING FROM THE MYERS REACTION TO A NEW THERMAL CYCLIZATION MODE IN ENYNE-ALLENES
SCHMITTEL, M
STRITTMATTER, M
KIAU, S
[J]. TETRAHEDRON LETTERS, 1995, 36 (28) : 4975 - 4978
[8] A CONVENIENT SYNTHESIS OF ACYCLIC CONJUGATED ENEDIYNES
SHIBUYA, M
SAKAI, Y
NAOE, Y
[J]. TETRAHEDRON LETTERS, 1995, 36 (06) : 897 - 898
[9] STEREOSELECTIVE SYNTHESIS OF ENEDIYNES AND ENYNE-ALLENES HAVING A TETRASUBSTITUTED CENTRAL CARBON-CARBON DOUBLE-BOND
WANG, ZG
WANG, KK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) : 4738 - 4742
[10] STUDIES ON DNA CLEAVING AGENTS - SYNTHESIS AND CHEMICALLY-INDUCED CYCLOAROMATIZATION OF A MONOCYCLIC NEOCARZINOSTATIN CHROMOPHORE ANALOG
WENDER, PA
TEBBE, MJ
[J]. TETRAHEDRON LETTERS, 1991, 32 (37) : 4863 - 4866

← 1 2 →