PREPARATION OF SOME NOVEL TRISUBSTITUTED 1,3,5-TRIAZINES AND HYBRID LINKER MODE 1,3,5-TRIAZINE DERIVATIVES AND THEIR BIOLOGICAL EVALUATION

被引：6

作者：

Mibu, Nobuko ^{[1
]}

Yokomizo, Kazumi ^{[2
]}

Yamada, Kanae ^{[1
]}

Matsuyama, Junko ^{[1
]}

Tomonaga, Syoko ^{[1
]}

Sakai, Izumi ^{[1
]}

Sato, Ryo ^{[1
]}

Kawano, Yuki ^{[1
]}

Matsumoto, Yumemi ^{[1
]}

Fujita, Yuka ^{[1
]}

Inoue, Yusuke ^{[1
]}

Iida, Masaya ^{[2
]}

Hashiguchi, Kaneto ^{[2
]}

Zhou, Jian-Rong ^{[2
]}

Furutachi, Makoto ^{[1
]}

Sumoto, Kunihiro ^{[1
]}

机构：

[1] Fukuoka Univ, Fac Pharmaceut Sci, Jonan Ku, 8-19-1 Nanakuma, Fukuoka, Fukuoka 8140180, Japan

[2] Sojo Univ, Fac Pharmaceut Sci, Nishi Ku, 4-22-1 Ikeda, Kumamoto 8600082, Japan

来源：

HETEROCYCLES | 2019年 / 98卷 / 04期

关键词：

ACID PINACOL ESTERS; CARBOHYDRATE-RECOGNITION; ANTIVIRAL ACTIVITIES; GLYCOCALYX; DISCOVERY;

D O I：

10.3987/COM-19-14052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a new route to the preparation of C-3-symmetrical multivalent hybrid-type molecules having a tris-aminoethylamine (TAEA) linker group and 1,3,5-triazine recognition moieties in the molecule and we also report the results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. Among the tested compounds, a new mid-size C-2-symmetrical multivalent hybrid-type molecule (10aq) showed a high level of anti-HSV-1 activity (EC50 = 19.7 mu M) with low cytotoxicity (CC50 > 200 mu M) against Vero cells. A new C-S-symmetrical multivalent derivative (4ab) also showed high anti-HSV-1 activity (EC50 = 1.77 mu M) with low cytotoxicity (CC50 > 200 mu M). The hybrid-type C-2-symmetrical multivalent mid-size molecule (10aq) seems to be an interesting new lead in the search for new hybrid-type symmetrical multivalent antiviral compounds.

引用

页码：489 / 508

页数：20

共 50 条

[1] SOME HYBRID LINKER MODE C2-SYMMETRICAL 1,3,5-TRIAZINE DERIVATIVES AND THEIR BIOLOGICAL EVALUATION
Mibu, Nobuko
Furutachi, Makoto
Inoue, Yusuke
Fujita, Yuka
Matsumoto, Yumemi
Kawano, Yuki
Tomonaga, Syoko
Matsuyama, Junko
Yamada, Kanae
Sato, Ryo
Yokomizo, Kazumi
Zhou, Jian-Rong
Shimomura, Shunsuke
Ota, Kaori
Sumoto, Kunihiro
[J]. HETEROCYCLES, 2019, 98 (11) : 1580 - 1588
[2] HYBRID LINKER MODE C2-SYMMETRICAL 1,3,5-TRIAZINE DERIVATIVES AND THEIR BIOLOGICAL EVALUATION
Shimomura, Shunsuke
Yokomizo, Kazumi
Zhou, Jian-Rong
Ota, Kaori
Mibu, Nobuko
Furutachi, Makoto
Sumoto, Kunihiro
[J]. HETEROCYCLES, 2021, 102 (12) : 2379 - 2390
[3] SYNTHESIS OF NITRO-1,3,5-TRIAZINES NITROSO-1,3,5-TRIAZINES AND AZOXY-1,3,5-TRIAZINES BY THE OXIDATION OF 2-HYDROXYAMINO-4,6-BIS(DIMETHYLAMINO)-1,3,5-TRIAZINE
SEDOVA, VF
KRIVOPALOV, VP
MAMAEV, VP
[J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1987, 36 (06): : 1327 - 1328
[4] Synthesis of some 1,3,5-triazine derivatives
Azarifar, D
Forghaniha, A
[J]. HETEROCYCLES, 2006, 68 (04) : 807 - 810
[5] Synthesis and biological evaluation of novel 1,3,5-triazine derivatives as antimicrobial agents
Zhou, Chunhui
Min, Jaeki
Liu, Zhigang
Young, Anne
Deshazer, Heather
Gao, Tian
Chang, Young-Tae
Kallenbach, Neville R.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (04) : 1308 - 1311
[6] TRIAZINES .11. SOME REACTIONS OF 1,3,5-TRIAZINE
GRUNDMANN, C
KREUTZBERGER, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (01) : 44 - 48
[7] TRIAZINES .6. 1,3,5-TRIAZINE
GRUNDMANN, C
KREUTZBERGER, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (02) : 632 - 633
[8] SOME SUBSTITUTED 1,3,5-TRIAZINES
FORBES, AD
GOULD, P
HILLS, IR
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1965, (FEB): : 1113 - &
[9] 1,3,5-TRIAZINES .X. COMPLEXES OF [2,4,6-TRISDIMETHYLAMINO-1,3,5-TRIAZINE
DAS, SK
GUNDUZ, T
SHAW, RA
SMITH, BC
[J]. JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1969, (09): : 1403 - &
[10] Trisubstituted 1,3,5-triazines. 2. Synthesis of 1,3,5-triazines on the basis of 2,4,6-tris[(tert-butoxycarbonyl)methylene]hexahydro-1,3,5-triazine
Shastin, AV
Godovikova, TI
Korsunsky, BL
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (10): : 1404 - 1407

← 1 2 3 4 5 →