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Home > Indoles and Oxindole > 13220-57-0
13220-57-0 | Indolo[2,1-b]quinazoline-6,12-dione
CAS No: 13220-57-0 Catalog No: AG0010E4 MDL No:MFCD00012073
Product Description
Catalog Number:
AG0010E4
Chemical Name:
Indolo[2,1-b]quinazoline-6,12-dione
CAS Number:
13220-57-0
Molecular Formula:
C15H8N2O2
Molecular Weight:
248.2362
MDL Number:
MFCD00012073
IUPAC Name:
indolo[2,1-b]quinazoline-6,12-dione
InChI:
InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H
InChI Key:
VQQVWGVXDIPORV-UHFFFAOYSA-N
SMILES:
O=C1c2nc3ccccc3c(=O)n2c2c1cccc2
NSC Number:
349447
Properties
Complexity:
471
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
248.059g/mol
Formal Charge:
0
Heavy Atom Count:
19
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
248.241g/mol
Monoisotopic Mass:
248.059g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
49.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.1
Literature
| Title | Journal |
|---|---|
| Aryl Hydrocarbon Receptor Activation Synergistically Induces Lipopolysaccharide-Mediated Expression of Proinflammatory Chemokine (c-c motif) Ligand 20. | Toxicological sciences : an official journal of the Society of Toxicology 20151101 |
| Tryptanthrin induces growth inhibition and neuronal differentiation in the human neuroblastoma LA-N-1 cells. | Chemico-biological interactions 20130425 |
| Design, synthesis, and structure-activity relationship studies of tryptanthrins as antitubercular agents. | Journal of natural products 20130322 |
| Tryptanthrin derivatives as Toxoplasma gondii inhibitors--structure-activity-relationship of the 6-position. | Bioorganic & medicinal chemistry letters 20130215 |
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Malassezia-derived indoles activate the aryl hydrocarbon receptor and inhibit Toll-like receptor-induced maturation in monocyte-derived dendritic cells. | The British journal of dermatology 20120901 |
| Synthesis of benzo-annulated tryptanthrins and their biological properties. | Bioorganic & medicinal chemistry 20120815 |
| Alkaloids from the root of Isatis indigotica. | Journal of natural products 20120622 |
| On the inhibition of 5-lipoxygenase product formation by tryptanthrin: mechanistic studies and efficacy in vivo. | British journal of pharmacology 20120201 |
| Tryptanthrin-loaded nanoparticles for delivery into cultured human breast cancer cells, MCF7: the effects of solid lipid/liquid lipid ratios in the inner core. | Chemical & pharmaceutical bulletin 20110101 |
| Proliferation-attenuating and apoptosis-inducing effects of tryptanthrin on human chronic myeloid leukemia K562 cell line in vitro. | International journal of molecular sciences 20110101 |
| Transport characteristics of tryptanthrin and its inhibitory effect on P-gp and MRP2 in Caco-2 cells. | Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques 20110101 |
| Cytotoxicity and reversal of multidrug resistance by tryptanthrin-derived indoloquinazolines. | Acta pharmacologica Sinica 20100201 |
| 2-Aminotryptanthrin derivative with pyrene as a FRET-based fluorescent chemosensor for Al3+. | Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20091201 |
| Downregulation of GSTpi expression by tryptanthrin contributing to sensitization of doxorubicin-resistant MCF-7 cells through c-jun NH2-terminal kinase-mediated apoptosis. | Anti-cancer drugs 20090601 |
| Inhibition of Toxoplasma gondii by indirubin and tryptanthrin analogs. | Antimicrobial agents and chemotherapy 20081201 |
| Isolation, structure elucidation, and synthesis of cytotoxic tryptanthrin analogues from Phaius mishmensis. | Journal of natural products 20080701 |
| One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine. | Chemical & pharmaceutical bulletin 20080401 |
| Recent patent reviews on small molecule-based antimalarial drugs. | Recent patents on anti-infective drug discovery 20071101 |
| Identification of a tryptanthrin metabolite in rat liver microsomes by liquid chromatography/electrospray ionization-tandem mass spectrometry. | Biological & pharmaceutical bulletin 20071001 |
| Tryptanthrin inhibits MDR1 and reverses doxorubicin resistance in breast cancer cells. | Biochemical and biophysical research communications 20070622 |
| Specific stabilization of DNA triple helices by indolo[2,1-b]quinazolin-6,12-dione derivatives. | Bioorganic & medicinal chemistry letters 20070315 |
| Quantification of active principles and pigments in leaf extracts of Isatis tinctoria by HPLC/UV/MS. | Planta medica 20070201 |
| Radical reactions with 3H-quinazolin-4-ones: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin. | Organic & biomolecular chemistry 20070107 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Anti-inflammatory and antiallergic activity in vivo of lipophilic Isatis tinctoria extracts and tryptanthrin. | Planta medica 20060501 |
| [Studies on chemical constituents in leaf of Isatis indigotica]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20051001 |
| HPLC based activity profiling for 5-lipoxygenase inhibitory activity in Isatis tinctoria leaf extracts. | Fitoterapia 20050601 |
| Inhibition of hepatocyte growth factor induction in human dermal fibroblasts by tryptanthrin. | Biological & pharmaceutical bulletin 20050201 |
| Prevention of experimentally induced irritant contact dermatitis by extracts of Isatis tinctoria compared to pure tryptanthrin and its impact on UVB-induced erythema. | Planta medica 20040501 |
| A comparative study on the skin penetration of pure tryptanthrin and tryptanthrin in Isatis tinctoria extract by dermal microdialysis coupled with isotope dilution ESI-LC-MS. | Planta medica 20030501 |
| Inhibitory activity of tryptanthrin on prostaglandin and leukotriene synthesis. | Planta medica 20021001 |
| Novel indolo[2,1-b]quinazoline analogues as cytostatic agents: synthesis, biological evaluation and structure-activity relationship. | Bioorganic & medicinal chemistry letters 20020902 |
| Analysis of stereoelectronic properties, mechanism of action and pharmacophore of synthetic indolo[2,1-b]quinazoline-6,12-dione derivatives in relation to antileishmanial activity using quantum chemical, cyclic voltammetry and 3-D-QSAR CATALYST procedures. | Bioorganic & medicinal chemistry 20020601 |
| The natural plant product tryptanthrin ameliorates dextran sodium sulfate-induced colitis in mice. | International immunopharmacology 20020301 |
| Quantitative determination of the dual COX-2/5-LOX inhibitor tryptanthrin in Isatis tinctoria by ESI-LC-MS. | Planta medica 20020201 |
| Identification and isolation of the cyclooxygenase-2 inhibitory principle in Isatis tinctoria. | Planta medica 20010701 |
| Cell differentiation and apoptosis of monocytic and promyelocytic leukemia cells (U-937 and HL-60) by tryptanthrin, an active ingredient of Polygonum tinctorium Lour. | Pathology international 20010501 |
| Antibacterial action of tryptanthrin and kaempferol, isolated from the indigo plant (Polygonum tinctorium Lour.), against Helicobacter pylori-infected Mongolian gerbils. | Journal of gastroenterology 20010101 |
| Prevention of azoxymethane-induced intestinal tumors by a crude ethyl acetate-extract and tryptanthrin extracted from Polygonum tinctorium Lour. | Anticancer research 20010101 |
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