Title:
GUANIDINOTHIAZOLE COMPOUND, AND PREPARATION METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/135613
Kind Code:
A1
Abstract:
Disclosed in the present invention are a guanidinothiazole compound, and a preparation method therefor and the use thereof. The structural formula of the guanidinothiazole compound is as shown in formula (IV). According to the present invention, a series of guanidinothiazole compounds of new structures are designed and synthesized by means of introducing a lipophilic side chain into the C2 position and hydrophilic guanidyl into the C5 position of a thiazole ring. The preparation method therefor comprises: performing a condensation reaction on an aldehyde compound (I) and thiosemicarbazide, which serve as as raw materials, to obtain a first-step product (II); reacting the first-step product (II) with 3-chloroacetylacetone to obtain a second-step product (III); and reacting the second-step product (III) with aminoguanidine hydrochloride to prepare a final product (IV). The guanidinothiazole compound exhibits an antibacterial activity, and especially has a good antibacterial activity on Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa, which compound can be used as an antibacterial candidate compound.
Inventors:
XIE XIAOBAO (CN)
YANG PING (CN)
SHI QINGSHAN (CN)
HUANG XIAOMO (CN)
SHU XIULIN (CN)
YANG PING (CN)
SHI QINGSHAN (CN)
HUANG XIAOMO (CN)
SHU XIULIN (CN)
Application Number:
PCT/CN2022/073431
Publication Date:
June 30, 2022
Filing Date:
January 24, 2022
Export Citation:
Assignee:
INST OF MICROBIOLOGY GUANGDONG ACADEMY OF SCIENCES GUANGDONG DETECTION CENTER OF MICROBIOLOGY (CN)
International Classes:
C07D277/50; A01N47/44; A01P1/00; A61K31/426; A61P31/04
Foreign References:
| CN113336720A | 2021-09-03 | |||
| CN112645897A | 2021-04-13 |
Other References:
OMAR ABDELSATTAR M., IHMAID SALEH, HABIB EL-SAYED E., ALTHAGFAN SULTAN S., AHMED SAHAR, ABULKHAIR HAMADA S., AHMED HANY E.A.: "The rational design, synthesis, and antimicrobial investigation of 2-Amino-4-Methylthiazole analogues inhibitors of GlcN-6-P synthase", BIOORGANIC CHEMISTRY, ACADEMIC PRESS INC., NEW YORK, NY., US, vol. 99, 1 June 2020 (2020-06-01), US , pages 1 - 12, XP055945107, ISSN: 0045-2068, DOI: 10.1016/j.bioorg.2020.103781
OMAR, ABDELSATTAR M. ET AL.: "Novel molecular discovery of promising amidine-based thiazole analogues as potent dual Matrix Metalloproteinase-2 and 9 inhibitors: Anticancer activity data with prominent cell cycle arrest and DNA fragmentation analysis effects.", BIOORGANIC CHEMISTRY, vol. 101, 2 June 2020 (2020-06-02), XP086227729, ISSN: 0045-2068, DOI: 10.1016/j.bioorg.2020.103992
OMAR, ABDELSATTAR M. ET AL.: "Novel molecular discovery of promising amidine-based thiazole analogues as potent dual Matrix Metalloproteinase-2 and 9 inhibitors: Anticancer activity data with prominent cell cycle arrest and DNA fragmentation analysis effects.", BIOORGANIC CHEMISTRY, vol. 101, 2 June 2020 (2020-06-02), XP086227729, ISSN: 0045-2068, DOI: 10.1016/j.bioorg.2020.103992
Attorney, Agent or Firm:
GUANGZHOU KEYUE I.P. LAW OFFICE (CN)
Download PDF: