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
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
收藏
页数:6
相关论文
共 50 条
  • [41] Synthesis of pyrano[2,3-d]pyrimidine scaffolds promoted by polyfluorinated alcohol as a reusable solvent/catalyst
    Mohamadpour, Farzaneh
    RESULTS IN CHEMISTRY, 2024, 8
  • [42] One-pot synthesis of pyrano[2,3-d]pyrimidine derivatives in ionic liquid medium
    Li, YL
    Du, BX
    Wang, XS
    Shi, DQ
    Tu, SJ
    JOURNAL OF CHEMICAL RESEARCH, 2006, (03) : 157 - 159
  • [43] Nano CuO-Ag-catalyzed synthesis of some novel pyrano[2,3-d] pyrimidine derivatives and evaluation of their bioactivity
    Poola, Sreelakshmi
    Shaik, Mahammad S.
    Sudileti, Murali
    Yakkate, Subbarao
    Nalluri, Vedasree
    Chippada, Apparao
    Cirandur, Suresh R.
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2020, 67 (05) : 805 - 820
  • [44] Synthesis and antibacterial activity of novel pyrano[2,3-d]pyrimidine-4-one–3-phenylisoxazole hybrids
    B. S. Kumar
    P. V. A. Lakshmi
    B. S. Veena
    E. Sujatha
    Russian Journal of General Chemistry, 2017, 87 : 829 - 836
  • [45] Green Method Synthesis of Pyrano[2,3-d]Pyrimidine Derivatives: Antimicrobial and Electrochemical Behavior Studies
    Badiger, Krishnappa B.
    Kamanna, Kantharaju
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (07) : 5976 - 5995
  • [46] ACTIVATED NITRILES IN HETEROCYCLIC SYNTHESIS - NOVEL SYNTHESES OF PYRANO[2,3-B]PYRIDINES AND PYRANO[2,3-D]PYRIMIDINES
    ELGEMEIE, GEH
    ELKERIM, A
    GOHAR, M
    REGAILA, HA
    ELFAHHAM, HA
    ARCHIV DER PHARMAZIE, 1988, 321 (03) : 131 - 133
  • [47] Synthesis and Antimicrobial Activity of some Tetrahydro Quinolone Diones and Pyrano[2,3-d]pyrimidine Derivatives
    Shahi, Masoume
    Foroughifar, Naser
    Mobinikhaledi, Akbar
    IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH, 2015, 14 (03): : 757 - 763
  • [48] Synthesis, antimicrobial activity and molecular docking studies of pyrano[2,3-d]pyrimidine formimidate derivatives
    Kotaiah Yalagala
    Suresh Maddila
    Surjyakanta Rana
    Surya Narayana Maddila
    Sukesh Kalva
    Adam Arnold Skelton
    Sreekantha Babu Jonnalagadda
    Research on Chemical Intermediates, 2016, 42 : 3763 - 3774
  • [49] Synthesis, antimicrobial activity and molecular docking studies of pyrano[2,3-d]pyrimidine formimidate derivatives
    Yalagala, Kotaiah
    Maddila, Suresh
    Rana, Surjyakanta
    Maddila, Surya Narayana
    Kalva, Sukesh
    Skelton, Adam Arnold
    Jonnalagadda, Sreekantha Babu
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (04) : 3763 - 3774
  • [50] DABCO promoted one-pot synthesis of dihydropyrano(c)chromene and pyrano [2,3-d]pyrimidine derivatives and their biological activities
    Jain, Shubha
    Paliwal, Pradeep K.
    Babu, G. Neelaiah
    Bhatewara, Anjna
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2014, 18 (05) : 535 - 540