BIOMAT Database Logo BIOMAT Database Logo

Synthesis and biological activities of 2-amino-thiazole-5-carboxylic acid phenylamide derivatives. 2011

Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, P.R. China.

In an attempt to develop potent and selective anti-tumor drugs, a series of novel 2-amino-thiazole-5-carboxylic acid phenylamide derivatives were designed based on the structure of dasatinib. All compounds were synthesized by a systematic combinatorial chemical approach. Biological evaluation revealed that N-(2-chloro-6-methylphenyl)-2-(2-(4-methylpiperazin-1-yl)acetamido)thiazole-5-carboxamide (6d) exhibited high antiproliferative potency on human K563 leukemia cells comparable to dasatinib. Against mammary and colon carcinoma cells 6d was either inactive (MDA-MB 231) or distinctly less active (MCF-7 and HT-29: IC(50) = 20.2 and 21.6 µM, respectively). Dasatinib showed at each cell line IC(50) < 1 µM. The results of this structure activity relationship study clearly documented that the pyrimidin-4-ylamino core of dasatinib is responsible for the anti-tumor activity against non-leukemia cell lines.

UI MeSH Term Description Entries
D007938 Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006) Leucocythaemia,Leucocythemia,Leucocythaemias,Leucocythemias,Leukemias
D011743 Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D001943 Breast Neoplasms Tumors or cancer of the human BREAST. Breast Cancer,Breast Tumors,Cancer of Breast,Breast Carcinoma,Cancer of the Breast,Human Mammary Carcinoma,Malignant Neoplasm of Breast,Malignant Tumor of Breast,Mammary Cancer,Mammary Carcinoma, Human,Mammary Neoplasm, Human,Mammary Neoplasms, Human,Neoplasms, Breast,Tumors, Breast,Breast Carcinomas,Breast Malignant Neoplasm,Breast Malignant Neoplasms,Breast Malignant Tumor,Breast Malignant Tumors,Breast Neoplasm,Breast Tumor,Cancer, Breast,Cancer, Mammary,Cancers, Mammary,Carcinoma, Breast,Carcinoma, Human Mammary,Carcinomas, Breast,Carcinomas, Human Mammary,Human Mammary Carcinomas,Human Mammary Neoplasm,Human Mammary Neoplasms,Mammary Cancers,Mammary Carcinomas, Human,Neoplasm, Breast,Neoplasm, Human Mammary,Neoplasms, Human Mammary,Tumor, Breast
D003110 Colonic Neoplasms Tumors or cancer of the COLON. Cancer of Colon,Colon Adenocarcinoma,Colon Cancer,Cancer of the Colon,Colon Neoplasms,Colonic Cancer,Neoplasms, Colonic,Adenocarcinoma, Colon,Adenocarcinomas, Colon,Cancer, Colon,Cancer, Colonic,Cancers, Colon,Cancers, Colonic,Colon Adenocarcinomas,Colon Cancers,Colon Neoplasm,Colonic Cancers,Colonic Neoplasm,Neoplasm, Colon,Neoplasm, Colonic,Neoplasms, Colon
D005260 Female Females
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000069439 Dasatinib A pyrimidine and thiazole derived ANTINEOPLASTIC AGENT and PROTEIN KINASE INHIBITOR of BCR-ABL KINASE. It is used in the treatment of patients with CHRONIC MYELOID LEUKEMIA who are resistant or intolerant to IMATINIB. (18F)-N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide,BMS 354825,BMS-354825,BMS354825,N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide,Sprycel,354825, BMS
D000577 Amides Organic compounds containing the -CO-NH2 radical. Amides are derived from acids by replacement of -OH by -NH2 or from ammonia by the replacement of H by an acyl group. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amide
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

Related Publications

Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Substituted 5-aroylpyrazine-2-carboxylic acid derivatives: synthesis and biological activity.
November 2003, Farmaco (Societa chimica italiana : 1989),
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Structure-activity relationship of indoline-2-carboxylic acid N-(substituted)phenylamide derivatives.
August 2010, Bioorganic & medicinal chemistry letters,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Asymmetric synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives.
September 2001, The Journal of organic chemistry,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Synthesis of 5-fluoro-2'-deoxyuridine-5'-carboxylic acid and its derivatives.
January 1969, Journal of medicinal chemistry,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Design, synthesis, and biological activity of novel 4-(3,4-dimethoxyphenyl)-2-methylthiazole-5-carboxylic acid derivatives.
June 2004, Bioorganic & medicinal chemistry,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Design, synthesis, and biological evaluation of benzofuran- and 2,3-dihydrobenzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents and inhibitors of NF-κB.
June 2015, Bioorganic & medicinal chemistry letters,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
[Synthesis of derivatives of xanthene-2-carboxylic acid and xanthone-2-carboxylic acid].
January 1984, Yao xue xue bao = Acta pharmaceutica Sinica,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Amino acids and derivatives of thiazole-4-carboxylic acid as constituents of thiopeptin B.
May 1977, The Journal of antibiotics,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Synthesis and biological properties of derivatives of 3-methyl-5-aminoisothiazolo-4-carboxylic acid.
January 1976, Archivum immunologiae et therapiae experimentalis,
Wukun Liu, and Jinpei Zhou, and Fan Qi, and Kerstin Bensdorf, and Zhiyu Li, and Huibin Zhang, and Hai Qian, and Wenlong Huang, and Xueting Cai, and Peng Cao, and Anja Wellner, and Ronald Gust
Recent Literature on the Synthesis of Thiazole Derivatives and their Biological Activities.
January 2024, Mini reviews in medicinal chemistry,
Copied contents to your clipboard!