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Tetrahydrocarbazole derivative as well as preparation method and application thereof

A technology for tetrahydrocarbazole and derivatives is applied in the field of tetrahydrocarbazole derivatives and their preparation, which can solve the problems of unsatisfactory anti-tuberculosis effect and drug resistance, and achieve excellent anti-tuberculosis effects, The effect of less side reactions and high yield

Pending Publication Date: 2022-05-31
SHENZHEN BAY LAB +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of this application is to overcome the above-mentioned deficiencies in the prior art, provide a tetrahydrocarbazole derivative and its preparation method, to solve the existing anti-tuberculosis drugs have unsatisfactory anti-tuberculosis Mycobacterium effect or lead to the existence of drug resistance, etc. Insufficient technical issues

Method used

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  • Tetrahydrocarbazole derivative as well as preparation method and application thereof
  • Tetrahydrocarbazole derivative as well as preparation method and application thereof
  • Tetrahydrocarbazole derivative as well as preparation method and application thereof

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preparation example Construction

[0039] On the other hand, the examples of the present application provide the preparation methods of the tetrahydrocarbazole derivatives in the examples of the above-mentioned application. The preparation method of the tetrahydrocarbazole derivative of the embodiment of the present application comprises the following steps:

[0040] S01: the following structural formula I A The reactant A shown is with the following structural formula I B The shown reactant B and the base catalyst carry out the first substitution reaction in the first reaction solvent to generate the following structural formula I Z1 the first intermediate product shown;

[0041]

[0042] S02: the first intermediate product is reversely carried out redox reaction with reducing agent and acid additive in the second reaction solvent to generate the following structural formula I Z2 the second intermediate product shown;

[0043]

[0044] S03: combine the second intermediate product with the following s...

Embodiment 1

[0094] This embodiment provides a 2,3,4,9-tetrahydrocarbazole derivative and a preparation method thereof. The structural formula of the 2,3,4,9-tetrahydrocarbazole derivative is the above formula I 1 shown.

[0095] Formula I above 1 The preparation method of the 2,3,4,9-tetrahydrocarbazole derivatives shown comprises the following steps:

[0096] S1: Synthesis of Reactants A3 and A above:

[0097] Synthesis of reactant A3: According to the synthetic route shown in the above reaction formula (1), in a 1000 mL round-bottomed flask, 30 g of 4-nitro-5-fluorophenylhydrazine, 21 g of 1,2-cyclohexanedi 700 mL of ketone and 1M hydrochloric acid solution, then refluxed and stirred for 12 hours; cooled and filtered to obtain crude product 1, which was directly carried out to the next step without purification.

[0098] The synthesis of reactant A: according to the synthetic route shown in the above reaction formula (1), to the synthetic reactant A3 crude product was added concentr...

Embodiment 2

[0109] This embodiment provides a 2,3,4,9-tetrahydrocarbazole derivative and a preparation method thereof. The structural formula of the 2,3,4,9-tetrahydrocarbazole derivative is the above formula I 2 shown.

[0110] Formula I above 2 The preparation method of the 2,3,4,9-tetrahydrocarbazole derivatives shown comprises the following steps:

[0111] S1: The synthesis of reactant A3 and reactant A are respectively synthesized with reference to step S1 in Example 1:

[0112] S2: Synthesize the above structural formula I with reference to step S2 in Example 1 Z1 The first intermediate product shown. The difference is that the reactant p-fluorobenzyl bromide is replaced with p-nitrobenzyl bromide.

[0113] S3: Synthesize the above structural formula I with reference to step S3 in Example 1 Z3 The second intermediate product shown.

[0114] S4: Synthesize the above structural formula I with reference to step S4 in Example 1 Z3 The third intermediate product shown. The diffe...

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Abstract

The invention discloses a tetrahydrocarbazole derivative as well as a preparation method and application thereof. The molecular structural formula of the tetrahydrocarbazole derivative is as shown in the general formula I in the specification. Through the design of the molecular structure, the tetrahydrocarbazole derivative has an excellent anti-tubercle bacillus effect, the anti-tubercle bacillus effect of the tetrahydrocarbazole derivative is even excellent in isoniazide, and the tetrahydrocarbazole derivative does not generate drug resistance to most tubercle bacillus. The preparation method is high in target product yield, few in side reaction and easy in process condition control, and the prepared tetrahydrocarbazole derivative is stable in yield and performance.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a tetrahydrocarbazole derivative and a preparation method and application thereof. Background technique [0002] Tuberculosis (TB) is an airborne infectious disease caused by its pathogen, Mycobacterium tuberculosis. At present, drug-resistant tuberculosis, especially multi-drug-resistant and extensively drug-resistant tuberculosis, poses a serious threat to human health and even life, and has become a major challenge facing the world. According to the World Health Organization (WHO), tuberculosis has become the number one deadly infectious disease. my country is one of the countries with high TB ​​burden in the world and one of the countries with the most serious TB drug resistance problem. [0003] Folic acid is involved in the synthesis of nucleic acids and proteins, and is an important target of anti-tuberculosis drugs. DHFR (dihydrofolate reductase...

Claims

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Application Information

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IPC IPC(8): C07D209/88C07D409/14C07D401/14A61K31/403A61K31/4439A61K31/444A61P31/06
CPCC07D209/88C07D409/14C07D401/14A61P31/06
Inventor 陈杰安陈学明蒋晨然刘运尹登
Owner SHENZHEN BAY LAB
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