Novel bisamides derivative and preparation method and application thereof

A technology of bisamides and derivatives, which is applied in the field of preparation of new compounds, and can solve the problems that the application of bisamide derivatives with anti-tumor activity has not yet been reported.

Inactive Publication Date: 2015-03-11
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the prior art, the preparation of novel bisamide derivatives as shown in the pres

Method used

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  • Novel bisamides derivative and preparation method and application thereof
  • Novel bisamides derivative and preparation method and application thereof
  • Novel bisamides derivative and preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0054] N 1 -(5-(2,2-dichloroacetyl)-2-methylphenyl)-3-iodo-N 2 -Synthesis of (2-methyl-1-(1-thiomethyl)-2-propyl)phthalamide (derivative 01):

[0055]Step A: Preparation of 2-iodo-6-carboxy-N-(1,1-dimethyl-2-methylthioethyl)benzamide

[0056] 3-Iodophthalic anhydride (2.74g), 1-methylthio-2-methyl-2-aminopropane (1.19g) and triethylamine (1.00g) were mixed and dissolved in an appropriate amount of dichloromethane. The reaction mixture was stirred and reacted for 12 h, and worked up to obtain 2-iodo-6-carboxy-N-(1,1-dimethyl-2-methylthioethyl)benzamide as a yellow solid. Yield 75%, m.p. 127-128°C.

[0057] Step B: Preparation of N-acetyl-2-methylaniline.

[0058] 2-Methylaniline (5.1g), triethylamine (10.1g) and acetyl chloride (3.9g) were dissolved in an appropriate amount of dichloromethane, and stirred at room temperature for 2h. Workup gave N-acetyl-2-methylaniline. Yield 95%, m.p.108-109°C.

[0059] Step C: Preparation of N-(5-(2,2-dichloroacetyl)-2-methylphenyl)acet...

Embodiment 2

[0066] N 1 -(5-(2,2-dichloroacetyl)-2-methylphenyl)-3-iodo-N 2 -Synthesis of (2-methyl-1-(1-methylsulfonyl)-2-propyl)phthalamide (derivative 02):

[0067] Will N 1 -(5-(2,2-dichloroacetyl)-2-methylphenyl)-3-iodo-N 2 -(2-methyl-1-(1-thiomethyl)-2-propyl)phthalamide (0.30g), m-chloroperoxybenzoic acid (0.17g) were dissolved in tetrahydrofuran, stirred at room temperature , post-treatment yielded a white end product N 1 -(5-(2,2-dichloroacetyl)-2-methylphenyl)-3-iodo-N 2 -(2-Methyl-1-(1-methylsulfonyl)-2-propyl)phthalamide.

Embodiment 3

[0069] N 1 -(5-(2,2-dichloroacetyl)-2-methylphenyl)-3-iodo-N 2 Synthesis of -(2-methyl-1-(1-(N-aminocarbonylthiocarbonyl)methylthio)-2-propyl)phthalamide (derivative 03):

[0070] In an ice bath, N 1 -(5-(2,2-dichloroacetyl)-2-methylphenyl)-3-iodo-N 2 -(2-Methyl-1-(1-thiomethyl)-2-propyl)phthalamide (0.30g), iodobenzene acetate (0.134g), cyanamide (0.1g, 1.5mmol) Dissolve in tetrahydrofuran, heat up to room temperature and stir, and post-process to obtain a white solid N 1 -(5-(2,2-dichloroacetyl)-2-methylphenyl)-3-iodo-N 2 -(2-Methyl-1-(1-(N-aminocarbonylthiocarbonyl)methylthio)-2-propyl)phthalamide.

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Abstract

The invention relates to a novel bisamides derivative and a preparation method and an application thereof. A general formula of the novel bisamides derivative is shown as follows, and each group is shown in patent claims. The novel bisamides derivative has good antineoplastic activity, such as lung cancer, liver cancer and intestinal cancer. partial compound has higher in-vitro inhibition rate on three cancer cell bacterial strains than a control sample 5-fluorouracil, partial compound has in-vitro inhibition rate on lung adenocarcinoma (A549), liver cancer(Bel7402) and intestinal cancer (HCT-8) three cancer cell bacterial strains as high as more than 85%, and most compound has in-vitro inhibition rate on liver cancer (Bel7402) cell bacterial strain as high as more than 80%. The novel bisamides derivative can possibly be an antitumor drug.

Description

technical field [0001] The invention relates to a preparation method and application of a new compound, in particular to a preparation method of a novel bisamide derivative and its application as an antitumor drug. Background technique [0002] Tumor is a global problem faced by human beings, and the death rate caused by this fatal disease ranks first in the cause of human death. Chemotherapy plays a very important role in solving the problem of malignant tumors. For example, drugs directly acting on DNA: formylmerphalan, cyclophophamide, carmusrtin, camptothecin and its derivatives, etc.; anti-metabolism and anti-tumor drugs: 5-fluorouracil (5 -fluorouracil), cytarabine hydrochloride, etc.; anti-mitotic drugs and drugs based on tumor signal transduction mechanisms, etc. Scientists have been devoting themselves to discovering new and efficient anti-tumor drugs. In the prior art, there are no reports on the preparation of bisamide derivatives with novel structure and their...

Claims

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Application Information

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IPC IPC(8): C07C323/42C07C319/20C07C317/28C07C315/04C07C335/40C07C233/76C07C231/02A61K31/166A61K31/277A61K31/17A61P35/00
Inventor 李正名陈有为刘艾林李玉新王宝雷潘里万莹莹刘敬波陈伟
Owner NANKAI UNIV
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