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Phenothiazine compound as well as preparation method and application thereof
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A technology of phenothiazines and compounds, applied in the field of phenothiazines and their preparation, to achieve the effects of high reaction yield, mild reaction conditions and simple operation
Pending Publication Date: 2021-08-17
ZHENGZHOU UNIV
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However, there is no report linking phenothiazine compounds with anti-tumor effects based on LSD1 targets to play an anti-tumor effect, so this study is of great value
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[0039] The preparation process of compound 4 to compound 21 is as follows:
[0049] The difference between embodiment 2 and embodiment 1 is that the piperazine in step (2) is replaced by N-methylpiperazine, the alkaline substance in step (4) is pyridine, sodiumhydroxide, and all the other are the same as embodiment 1 . Compound 5 was prepared with a yield of 81.4%.
[0050] 1 H NMR (400MHz, CDCl 3 )δ7.15–7.12(m,4H),6.92–6.87(m,4H),3.92(t,J=6.9Hz,2H),2.50–2.47(m,10H),2.28(s,3H),1.99 –1.92(m,2H). 13 C NMR (100MHz, CDCl 3 )δ145.21, 127.44, 127.21, 125.07, 122.42, 115.51, 55.59, 54.99, 53.06, 45.87, 45.28, 24.38. HRMS (ESI) calcd for C 20 h 26 N 3 S[M+H] + ,340.1842; found, 340.1833.
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Abstract
The invention discloses a phenothiazine compound which has the advantages of novel structural general formula and framework, high efficiency, low toxicity and better inhibitory activity on LSD1. The invention also discloses a preparation method of the compound. The preparation method has the characteristics of mild reaction conditions, simplicity in operation and high reaction yield. According to the invention, phenothiazine is taken as a raw material, active groups are respectively introduced to a parent of phenothiazine, and new phenothiazine pharmacophores are synthesized; and phenothiazine compounds are designed and synthesized by modification with piperazine, morpholine, piperidine and other groups. The compound retains the activity of phenothiazine and also has the characteristics of modification groups, so that the biological activity of original molecules is improved, and the anti-tumor activity of target molecules is improved. The invention also discloses an application of the compound in preparation of LSD1-targeted antitumor drugs, and the compound shows good inhibitory activity on LSD1 and shows good development potential.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a phenothiazine compound and its preparation method and application. Background technique [0002] Epigenetics refers to the heritable changes that occur in genetic genes without changing the DNA sequence, including DNA modification, histone modification, non-coding RNA, and nucleosome remodeling. Abnormal epigenetic regulation can lead to misexpression of genes, causing various diseases and even tumors. Histone modification is an important research direction, including acetylation, methylation, phosphorylation, hydroxylation and ubiquitination, among which acetylation and methylation are the most important. Studies have shown that they have a regulatory effect on the transcription of genes. In 2004, the first histonelysinedemethylase 1 (Lysine Specific Demethylase 1, LSD1) was discovered, confirming that histonedemethylation is a reversible process. The level of methylatio...
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