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A kind of pyrimidine-piperazine-1,2,4-triazole derivative and its preparation method and application
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A technology for triazoles and derivatives, which is applied in the field of pyrimidine-piperazine-1,2,4-triazole derivatives and their preparation, can solve the problems that the related mechanism research is not very clear, and achieve excellent inhibitory effect, The effect of inhibiting protein capacity
Active Publication Date: 2022-07-26
CHENGDU NORMAL UNIV
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However, the research on the relevant mechanism is still not very clear
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Embodiment 1
[0055] A preparation method of pyrimidine-piperazine-1,2,4-triazole derivatives, comprising the following steps:
[0056] (1) Synthesis of (R)-2-aminobutyric acid methyl ester hydrochloride
[0057] (R)-2-aminobutyric acid (6.18g, 60mmol, 1.0eq) was dissolved in 100mL (40eq) methanol solution, placed in an ice-water bath under nitrogen protection, and thionyl chloride (14.28g) was slowly added , 120mmol, 2.0eq); after the dropwise addition is completed, transfer to a 70 ℃ oil bath, the reaction is refluxed for 1-2h, after TLC detects that the reaction is complete, after the reaction solution is cooled, the reaction solvent is distilled off under reduced pressure; using dichloromethane The methane was repeatedly dissolved and spin-dried for 2-3 times to obtain a white crystalline product with a yield of 99%.
[0058]
[0059] (2) Preparation of Intermediate I
[0060] At room temperature, (R)-2-aminobutyric acid methyl ester hydrochloride (1.0eq) was dissolved in DCM, foll...
Embodiment 2
[0078] Referring to the synthesis method of Example 1, changing the molar ratio of the substituent of the substrate and the reactant, compound 2 was obtained. Its nuclear magnetic data are: δ: 8.60(s, 1H), 7.62(s, 1H), 5.24(s, 1H), 2.81(m, 1H), 2.68(m, 2H), 2.62(m, 1H), 1.95 (m, 2H), 1.84-1.56 (m, 14H), 0.98 (m, 3H), 0.92 (m, 3H).
Embodiment 3
[0080] Referring to the synthesis method of Example 1, changing the molar ratio of the substituents of the substrate and the reactants, compound 3 was obtained. Its nuclear magnetic data are: δ: 8.64(s, 1H), 7.68(s, 1H), 6.40(d, J=7, 8Hz, 2H), 6.12(d, J=7, 8Hz, 2H), 5.94(s , 1H), 3.81(m, 1H), 2.62(m, 1H), 2.26(s, 3H), 1.95(m, 2H), 1.84-1.63(m, 8H), 0.96(m, 3H).
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Abstract
The invention discloses a pyrimidine-piperazine-1,2,4-triazole derivative and a preparation method and application thereof. The structural formula of the compound is: wherein, R 1 For chain or cyclic aliphatic hydrocarbon group, aromatic hydrocarbon group; R 2 It is a chain or cyclic aliphatic hydrocarbon group; R 3 is H or C1-C4 alkyl; R 4 It is a chain or cyclic aliphatic hydrocarbon group, an aromatic hydrocarbon group, a saturated heterocyclic substituent or an aromatic heterocyclic substituent. The compound prepared by the invention can effectively inhibit the expression of BRD4 protein, and can be used for preparing BRD4 protein inhibitor or corresponding therapeutic drug.
Description
technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and particularly relates to a pyrimidine-piperazine-1,2,4-triazole derivative and a preparation method and application thereof. Background technique [0002] BRD4 protein is a member of the BET protein family and was originally called MCAP (mitotic chromosome-associated protein), also known as Fshrg4 and Hunk1. BRD4 was discovered in 1988 when studying mammalian regulatory complexes. BRD4 contains three isoforms with different lengths: the long isoform contains 1362 residues, and the two short isoforms contain 722 and 796 residues, respectively. BRD4 contains two N-terminal BRDs domains (BD1 and BD2) and an outer terminal domain (ETD) and a C-terminal domain (CTD). Each BRD domain of BRD4 is composed of four left-handed α-helix bundles, αZ, αA, αB, and αC; ZA Loop and BC Loop are connected between αZ and αA helices, and between αB and αC helices , and constitute the acety...
Claims
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