Comprehensive Synthesis of Photoreactive (3-Trifluoromethyl)diazirinyl Indole Derivatives from 5- and 6-Trifluoroacetylindoles for Photoaffinity Labeling

被引：29

作者：

Murai, Yuta ^{[1
]}

Masuda, Katsuyoshi

Sakihama, Yasuko ^{[1
]}

Hashidoko, Yasuyuki ^{[1
]}

Hatanaka, Yasumaru ^{[2
]}

Hashimoto, Makoto ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Agr, Kita Ku, Sapporo, Hokkaido 0608589, Japan

[2] Toyama Univ, Grad Sch Med & Pharmaceut Sci, Toyama 9300194, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 19期

关键词：

EFFICIENT SYNTHESIS; ACID; CHEMISTRY; TRYPTOPHAN; DISCOVERY; LIGANDS; POTENT;

D O I：

10.1021/jo301552m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5- and 6-trifluoromethyldiazirinyl indoles were synthesized from corresponding bromoindole derivatives for the first time. They acted as mother skeletons for the comprehensive synthesis of various bioactive indole metabolites. These can be used in biological functional analysis as diazirine-based photoaffinity labels.

引用

页码：8581 / 8587

页数：7

共 50 条

[21] Synthesis of N-aminoindole ureas from ethyl 1-amino-6-(trifluoromethyl)-1H-indole-3-carboxylate
Belley, M
Scheigetz, J
Dubé, P
Dolman, S
SYNLETT, 2001, (02) : 222 - 225
[22] Synthesis and Characterisation of 5-(6-substituted phenyl-2H-chromen-3-yl) Oxazole Derivatives
Sadanandam, Palle
Sathaiah, Nomula
Jyothi, Vantikommu
Chari, Murugulla A.
Shobha, Donthabakthuni
Das, Parthasarathi
Mukkanti, Khagga
LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (09) : 683 - 690
[23] Synthesis of 5-(Benzylamino)-exo-3-azatricyclo-[5.2.1.02,6]decan-4-one derivatives
Vlasova, L. I.
Faizullina, S. S.
Lobov, A. N.
Kukovinets, O. S.
Dokichev, V. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (12) : 1792 - 1796
[24] Synthesis of 5-(Benzylamino)-exo-3-azatricyclo-[5.2.1.02,6]decan-4-one derivatives
L. I. Vlasova
S. S. Faizullina
A. N. Lobov
O. S. Kukovinets
V. A. Dokichev
Russian Journal of Organic Chemistry, 2016, 52 : 1792 - 1796
[25] ARYLSULFONIC ACID-DERIVATIVES .6. SYNTHESIS OF 4-SULFANILAMIDO-DERIVATIVES OF 5-(3-CARBETHOXY-4-ALKOXYBENZYL)PYRIMIDINES
GRIGORYAN, LA
KALDRIKYAN, MA
AROYAN, AA
ARMYANSKII KHIMICHESKII ZHURNAL, 1975, 28 (06): : 486 - 490
[26] Synthesis and herbicidal activity of 2-(3-(trifluoromethyl)-5-(alkoxy)-1H-pyrazol-1-yl)-4-aryloxypyrimidine derivatives
Liu, Wei-Min
Zhu, You-Quan
Wang, Yi-Feng
Liu, Bin
Zou, Xiao-Mao
Yang, Hua-Zheng
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (04) : 967 - 971
[27] SYNTHESIS OF 3,7-DIMETHYL-9-(4'-(3H-DIAZIRINYL)-2',6'-DIMETHYLPHENYL)-2E, 4E, 6E, 8E-NONATETRAENAL-1-H-3, A PHOTOAFFINITY-LABELING ANALOG OF ALL-TRANS-RETINAL
SONNEWALD, U
SELTZER, S
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1987, 24 (07): : 787 - 795
[28] 4-Halo-N-(5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)benzamide and Benzothioamide Derivatives: Synthesis and in vitro Anticancer Assessment
Aliabadi, Ali Reza
Harasami Neek, Hojat
Bahmani, Yazdan
IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2020, 39 (05): : 35 - 44
[29] SYNTHESIS AND STUDY OF THIOCARBOHYDRAZIDE DERIVATIVES .6. SYNTHESIS AND CYCLIZATION OF SUBSTITUTED OF 1-(3-METHYLBENZOTHIAZOLINIDENE-2)-5-(PHENYLAMIDOTHIOCARBO)-THIOCARBOHYDRAZIDE
DUBENKO, RG
BAZAVOVA, IM
PELKIS, PS
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1971, (05): : 603 - &
[30] Multicomponent synthesis and anticancer activity studies of novel 6-(Trifluoromethyl)-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylate derivatives
Valeru, Anil
Luo, Zhi-Bin
Khan, Imran
Liu, Bin
Sngepu, Bhavanarushi
Godumagadda, Narender Reddy
Xu, Yin
Xie, Jimin
SYNTHETIC COMMUNICATIONS, 2018, 48 (17) : 2226 - 2231

← 1 2 3 4 5 →