Rutaecarpine

Base Information

• Chemical Name: Rutaecarpine
• CAS No.: 84-26-4
• Molecular Formula: C18H13N3O
• Molecular Weight: 287.321
• Hs Code.: 29339900
• European Community (EC) Number: 635-907-6
• NSC Number: 258317
• UNII: 8XZV289PRY
• DSSTox Substance ID: DTXSID00232884
• Nikkaji Number: J4.894A,J3.210.250F
• Wikipedia: Rutecarpine
• Wikidata: Q15424771
• Pharos Ligand ID: A88HY4UARGB1
• Metabolomics Workbench ID: 49692
• ChEMBL ID: CHEMBL85139
• Mol file: 84-26-4.mol

Synonyms:8,13-dihydroindolo(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one;rutaecarpine;rutecarpine

Chemical Property of Rutaecarpine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 259.5 - 260oC
• Refractive Index: 1.781
• Boiling Point: 550.072 °C at 760 mmHg
• PKA: 15.79±0.20(Predicted)
• Flash Point: 286.473 °C
• PSA: 50.68000
• Density: 1.456 g/cm³
• LogP: 3.10090
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 18 mg/mL clear yellow solution, soluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 287.105862047
• Heavy Atom Count: 22
• Complexity: 517

Purity/Quality:

99% ^*data from raw suppliers

Rutaecarpine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 45-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2C(=NC3=CC=CC=C3C2=O)C4=C1C5=CC=CC=C5N4
• General Description: Rutaecarpine, also known as Rutecarpine or Rhetine, is an alkaloid derived from Rutaceous plants with demonstrated potential as a topoisomerase inhibitor. Certain derivatives, such as 10-bromorutaecarpine and 3-chlororutaecarpine, exhibit strong inhibitory activity against both topoisomerase I and II, surpassing reference drugs like camptothecin and etoposide in efficacy. These properties highlight its potential as a candidate for developing novel anticancer therapeutics targeting DNA replication and transcription processes.

Technology Process of Rutaecarpine

There total 130 articles about Rutaecarpine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3b-trifluoromethyl-13b,14-dihydrorutaecarpine (95274-40-1) → rutaecarpine (84-26-4)

Guidance literature:

With hydroxide; In ethanol; water; for 0.75h;

Reference yield: 95.0%

(E)-6-(2-phenylhydrazono)-8,9-dihydro-6H-pyrido-[2,1-b]quinazolin-11(7H)-one (80776-66-5,81589-34-6,95610-41-6) → rutaecarpine (84-26-4)

Guidance literature:

With PPA; at 180 ℃;

DOI:10.1016/j.tetlet.2003.11.090

Reference yield: 94.0%

6-phenylhydrazono-6,7,8,9-tetrahydro-11H-pyrido<2,1-b>quinazolin-11-one (80776-66-5,81589-34-6,95610-41-6) → rutaecarpine (84-26-4)

Guidance literature:

With PPA; at 160 - 180 ℃; for 0.333333h;

upstream raw materials:

anthranilic acid

1-methoxy-4,9-dihydro-3H-β-carboline

3-[2-(1H-indol-3-yl)ethyl]-1H,3H-quinazoline-2,4-dione

6-phenyl-hydrazono-6,7,8,9-tetrahydro-11-oxo-11H-pyrido[2,1-b]-quinazoline-hydrochloride

Downstream raw materials:

anthranilic acid

Indole-2-carboxylic acid

aniline

Refernces

New topoisomerases inhibitors: Synthesis of rutaecarpine derivatives and their inhibitory activity against topoisomerases

10.1007/s12272-012-0504-1

This research aimed to synthesize rutaecarpine derivatives and evaluate their inhibitory activities against topoisomerase I and II, enzymes crucial in DNA replication and transcription. The study was driven by the potential of these alkaloids, isolated from Rutaceous plants, to serve as natural product-based cytotoxic agents. The researchers synthesized a series of rutaecarpine derivatives using methods such as Fischer indole synthesis, acetic anhydride-mediated condensation, and ozonolysis, involving chemicals like 2-amino-5-chlorobenzoic acid, piperidin-2-one, benzaldehyde, and phenylhydrazine-HCl. The conclusions drawn from the study were that among the tested compounds, 10-bromorutaecarpine and 3-chlororutaecarpine exhibited strong inhibitory activities against both topo I and II, with effects somewhat stronger than those of the reference drugs camptothecin (CPT) and etoposide. These findings suggest that these rutaecarpine derivatives could be potential candidates for further development as topoisomerase inhibitors for therapeutic applications.