Synthesis, in vitro А-Glucosidase, and acetylcholinesterase inhibitory activities of novel Indol-Fused Pyrano[2,3-D]Pyrimidine compounds

被引：4

作者：

Nguyen, Ha Thanh ^{[1
,2
]}

Tuan, Anh Nguyen ^{[1
]}

Thi, Tuyet Anh Dang ^{[1
,2
]}

Van, Ket Tran ^{[2
,3
]}

Giang, Le-Nhat-Thuy ^{[1
,2
]}

Thi, Phuong Hoang ^{[1
]}

Thi, Quynh Giang Nguyen ^{[1
,2
]}

Thi, Cham Ba ^{[1
,2
]}

Quang, Hung Tran ^{[1
,2
]}

Nguyen, Tuyen Van ^{[1
,2
]}

机构：

[1] Vietnam Acad Sci & Technol VAST, Inst Chem, 18 Hoang Quoc Viet, Hanoi, Vietnam

[2] Grad Univ Sci & Technol, VAST, 18 Hoang Quoc Viet, Hanoi, Vietnam

[3] Mil Technol Acad, 236 Hoang Quoc Viet, Hanoi, Vietnam

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2024年 / 98卷

关键词：

Indol-fused pyrano[2; d; pyrimidine; Diabetes mellitus; alpha-glucosidase inhibitors; AChE inhibitors; Multicomponent-component reaction; BIOLOGICAL EVALUATION; COMPLICATIONS TRIAL/EPIDEMIOLOGY; MULTICOMPONENT SYNTHESIS; DIABETES INTERVENTIONS; ALPHA-AMYLASE; DERIVATIVES; DESIGN;

D O I：

10.1016/j.bmcl.2023.129566

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In this study, new indol-fused pyrano[2,3-d]pyrimidines were designed and synthesized. These products were obtained in moderate to good yields and their structures were assigned by NMR, MS, and IR analysis. Afterwards, the biological important of the products was highlighted by evaluating in vitro for alpha-glucosidase inhibitory activity as well as acetylcholinesterase (AChE) inhibitory activity. Eleven products revealed substantial inhibitory activity against alpha-glucosidase enzyme, among which, two most potent products 11d,e were approximately 93-fold more potent than acarbose as a standard antidiabetic drug. Besides that, product 11k exhibited good AChE inhibition. The substituents on the 5-phenyl ring, attached to the pyran ring, played a critical role in inhibitory activities. The biological potencies have provided an opportunity to further investigations of indol-fused pyrano[2,3-d]pyrimidines as potential anti-diabetic agents.

引用

页数：6

共 50 条

[41] Synthesis of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives and their anticancer activity
Kurumurthy, C.
Rao, P. Sambasiva
Swamy, B. Veera
Kumar, G. Santhosh
Rao, P. Shanthan
Narsaiah, B.
Velatooru, L. R.
Pamanji, R.
Rao, J. Venkateswara
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (08) : 3462 - 3468
[42] Discovery of novel c-Met kinase inhibitors bearing a thieno[2,3-d]pyrimidine or furo[2,3-d]pyrimidine scaffold
Zhao, Ailing
Gao, Xin
Wang, Yuanxiang
Ai, Jing
Wang, Ying
Chen, Yi
Geng, Meiyu
Zhang, Ao
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (13) : 3906 - 3918
[43] Efficient method for the synthesis of novel substituted thieno[2,3-d]pyrimidine-4-carboxylic acids, their derivatization, and antimicrobial activity
Vlasova, Olena D.
Krolenko, Konstantin Yu.
Nechayev, Maxim A.
Shynkarenko, Pavlo E.
Kabachnyy, Volodymyr I.
Vlasov, Sergiy V.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (02) : 184 - 188
[44] Synthesis and Biological Activity Studies of Novel Pyrido[2,3-d]pyrimidines and Pyrido[2,3-d]triazines
Elsaedany, Samir Kamel
Zein, Mohamed AbdEllatif
AbdElRehim, Elsayed Mohmoud
Keshk, Reda Mohammed
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2021, 47 (02) : 552 - 560
[45] Facile synthesis and antitumor activity of novel 2-trifluoromethylthieno[2,3-d]pyrimidine derivatives
Song, Xin-Jian
Yang, Ping
Gao, Hui
Wang, Yan
Dong, Xing-Gao
Tan, Xiao-Hong
CHINESE CHEMICAL LETTERS, 2014, 25 (07) : 1006 - 1010
[46] Synthesis and Anticancer Activity of Functionalized Thieno[2,3-d]pyrimidine Compounds and Their Triazinyl and Tetrazinyl Derivatives
El-Sofany, Walaa I.
Othman, Dalia Ahmed A.
Mahran, Asma M.
May, El-Manawaty A.
El-Sayed, Wael A.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2020, 46 (03) : 393 - 402
[47] Efficient synthesis and cytotoxic activity of polysubstituted thieno[2,3-d]pyrimidine derivatives
Wang, Tianshuai
Wu, Fengxu
Luo, Lun
Zhang, Yan
Ma, Junkai
Hu, Yanggen
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1256
[48] Synthesis of potent anticancer thieno[2,3-d]pyrimidine derivatives
Kandeel, M. M.
Mounir, Ashraf A.
Refaat, Hanan M.
Kassab, Asmaa E.
JOURNAL OF CHEMICAL RESEARCH, 2012, (05) : 266 - 275
[49] The Novel Catalyst (Hypogallic Acid-Based Deep Eutectic Solvent) for Preparation of the New Compounds (Pyrano[2,3-d]Pyrimidines)
Monem, Arezo
Habibi, Davood
Goudarzi, Hadis
POLYCYCLIC AROMATIC COMPOUNDS, 2024, 44 (07) : 4531 - 4544
[50] Synthesis and in vitro antitumor evaluation of some new thiophenes and thieno[2,3-d]pyrimidine derivatives
Fouad, Mahasen M.
El-Bendary, Eman R.
Suddek, Ghada M.
Shehata, Ihsan A.
El-Kerdawy, Mohamed M.
BIOORGANIC CHEMISTRY, 2018, 81 : 587 - 598

← 1 2 3 4 5 →