Small molecule compound and synthesizing method and uses thereof
AssigneeTechnoderma Medicines Pte Ltd.
InventorsZengquan Wang, Sheldon Cao, Chen Mao
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Abstract
Provided is a small molecule compound as represented by structural formula (I). The product of the present invention in various concentrations and dosages can achieve an obvious change in the growth period of hairs, promoting the growth of the hairs, thus exhibiting an obvious effect of promoting hair growth. In addition, changes in the weight of a mouse in each group are slow, indicating that the test compound does not cause weight loss in an animal.
Claims11
A small molecule compound, characterized in that, it is represented by the following structural formula:
- R1 is selected from hydrogen, halogen, C1-C6alkyl or optionally substituted with 1-3 substituents, cyano, isocyanate, amide, iso-sulfonamide (SO2NHR), iso-sulfinyl (SONH), sulfonamide (NHSO2R), sulfonamido (NHSOR), S-alkyl, S-aryl, S-heteroaryl (SHet);
- wherein the substituents are selected from halogen, aryl, substituted aryl, heteroaryl, O-alkyl, O-aryl, O-heteroaryl, N-alkyl, N-aryl, N-heteroaryl;
- R2 is selected from Hydrogen, halogen, C1-C6 alkyl or substituted alkyl, alkoxy, aryl, substituted aryl, benzyl, substituted benzyl;
- R3 is selected from Hydrogen, halogen, C1-C6 alkyl or substituted alkyl, alkoxy, aryl, substituted aryl, benzyl, substituted benzyl;
- R4 is selected from hydrogen, C1-C6 alkyl or substituted alkyl;
- R5 is selected from hydrogen, C1-C6 alkyl or substituted alkyl;
- X is selected from alkylene or substituted alkylene, amino or substituted amino;
- Y is selected from alkylene or substituted alkylene, oxygen, sulfur, amino, carbonyl, sulfoxide, sulfone.
A process for synthesizing a small molecule compound, characterized in that:
- step 1:
- 4-methoxyphenol is reacted with 1,2,3-trichloro-5-nitrobenzene to form 1,3-dichloro-2-(4-methoxyphenoxy)-5-nitrobenzene;
- step 2:
- 1,3-dichloro-2-(4-methoxyphenoxy)-5-nitrobenzene is reacted with benzoic acid derivatives to form (5-(2,6-dichloro-4-nitrophenoxy)-2-methoxyphenyl) (substituted phenyl) methyl ketone);
- step 3:
- 1,3-dichloro-2-(3-(substituted benzyl)-4-methoxyphenoxy)-5-nitrobenzene is obtained from reduction of carbonyl of (5-(2,6-dichloro-4-nitrophenoxy)-2-methoxyphenyl)(substituted phenyl) methyl ketone to methylene;
- step 4:
- 3,5-dichloro-4-(3-(substituted benzyl)-4-methoxyphenoxy)-aniline is obtained from reduction of nitro of 1,3-dichloro-2-(3-(substituted benzyl)-4-methoxyphenoxy)-5-nitrobenzene to amino;
- Step 5:
- 3,5-dichloro-4-(3-(substituted benzyl)-4-methoxyphenoxy)-aniline is reacted with ethyl oxaloyl monochloride to form 2-((3,5-dichloro-4-(3-(substituted benzyl)-4-methoxyphenoxy)phenyl)amino)-oxoacetate;
- Step 6:
- 2-((3,5-dichloro-4-(3-(substituted benzyl)-4-methoxyphenoxy) phenyl)amino)-oxoacetate is reacted with hydroxylamine hydrochloride to form N1-(3,5-dichloro-4-(3-(substituted benzyl)-4-methoxyphenoxy)phenyl)-N2-oxalyl hydroxylamine;
- Step 7:
- after demethylation of methoxyl of N1-(3,5-dichloro-4-(3-(substituted benzyl)-4-methoxyphenoxy)phenyl)-N2-oxalyl hydroxylamine, a target small molecule compound can be obtained.
Dependencies are inferred from the claim text.