BIOMAT Database Logo BIOMAT Database Logo

Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors. 2013

Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.

Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors.

UI MeSH Term Description Entries
D011485 Protein Binding The process in which substances, either endogenous or exogenous, bind to proteins, peptides, enzymes, protein precursors, or allied compounds. Specific protein-binding measures are often used as assays in diagnostic assessments. Plasma Protein Binding Capacity,Binding, Protein
D002243 Carbolines A group of pyrido-indole compounds. Included are any points of fusion of pyridine with the five-membered ring of indole and any derivatives of these compounds. These are similar to CARBAZOLES which are benzo-indoles. Carboline,Pyrido(4,3-b)Indole,Beta-Carbolines,Pyrido(4,3-b)Indoles,Beta Carbolines
D004353 Drug Evaluation, Preclinical Preclinical testing of drugs in experimental animals or in vitro for their biological and toxic effects and potential clinical applications. Drug Screening,Evaluation Studies, Drug, Pre-Clinical,Drug Evaluation Studies, Preclinical,Drug Evaluations, Preclinical,Evaluation Studies, Drug, Preclinical,Evaluation, Preclinical Drug,Evaluations, Preclinical Drug,Medicinal Plants Testing, Preclinical,Preclinical Drug Evaluation,Preclinical Drug Evaluations,Drug Screenings,Screening, Drug,Screenings, Drug
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014364 Tryptophan An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals. Ardeydorm,Ardeytropin,L-Tryptophan,L-Tryptophan-ratiopharm,Levotryptophan,Lyphan,Naturruhe,Optimax,PMS-Tryptophan,Trofan,Tryptacin,Tryptan,Tryptophan Metabolism Alterations,ratio-Tryptophan,L Tryptophan,L Tryptophan ratiopharm,PMS Tryptophan,ratio Tryptophan
D050503 Indoleamine-Pyrrole 2,3,-Dioxygenase A dioxygenase with specificity for the oxidation of the indoleamine ring of TRYPTOPHAN. It is an extrahepatic enzyme that plays a role in metabolism as the first and rate limiting enzyme in the kynurenine pathway of TRYPTOPHAN catabolism. IDO Dioxygenase,Indolamine-2,3-Dioxygenase,Indoleamine 2,3-Dioxygenase,Indoleamine-Oxygen 2,3-Oxidoreductase (Decyclizing),Dioxygenase, IDO,Indolamine 2,3 Dioxygenase,Indoleamine 2,3 Dioxygenase

Related Publications

Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation.
May 2014, Organic & biomolecular chemistry,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Novel Substituted Tetrahydroquinoline Compounds as Indoleamine-2,3-dioxygenase (IDO) Inhibitors.
October 2021, ACS medicinal chemistry letters,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Design, synthesis and biological evaluation of novel aryl-acrylic derivatives as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors.
July 2019, Bioorganic & medicinal chemistry,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors.
February 2011, Bioorganic & medicinal chemistry,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Novel Substituted Piperazine Amide Compounds as Indoleamine-2,3-dioxygenase (IDO) Inhibitors.
November 2021, ACS medicinal chemistry letters,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Design, synthesis, and biological evaluation of 1,2,5-oxadiazole-3-carboximidamide derivatives as novel indoleamine-2,3-dioxygenase 1 inhibitors.
March 2020, European journal of medicinal chemistry,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Synthesis of novel tryptanthrin derivatives as dual inhibitors of indoleamine 2,3-dioxygenase 1 and tryptophan 2,3-dioxygenase.
June 2020, Bioorganic & medicinal chemistry letters,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Indoleamine 2,3-dioxygenase (IDO) inhibitors and cancer immunotherapy.
November 2022, Cancer treatment reviews,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Aminophenoxazinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis of exfoliazone and chandrananimycin A.
April 2013, Journal of medicinal chemistry,
Minoru Tanaka, and Xin Li, and Hidemasa Hikawa, and Takafumi Suzuki, and Katsuhiko Tsutsumi, and Masashi Sato, and Osamu Takikawa, and Hideharu Suzuki, and Yuusaku Yokoyama
Discovery and preliminary SARs of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors.
July 2011, European journal of medicinal chemistry,
Copied contents to your clipboard!