Rosabulin - Moligand™, ≥98% , CAS No.501948-05-6

CAS: 501948-05-6 Cat. No.: R648397 Molecular Weight: 400.45 PubChem CID: 9843935

GRADE & PURITY Moligand™, ≥98%

Synonyms

3-[(4-Cyanophenyl)methyl]-N-(3-methyl-5-isothiazolyl)-alpha-oxo-1-indolizineacetamide | 1-Indolizineacetamide, 3-((4-cyanophenyl)methyl)-N-(3-methyl-5-isothiazolyl)-alpha-oxo- | 2-[3-[(4-cyanophenyl)methyl]indolizin-1-yl]-N-(3-methyl-1,2-thiazol-5-yl)-2-o

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

In Vitro

Rosabulin (STA 5312) demonstrates substantial anti-proliferative activity against a wide range of cancer cell linesin vitro, including hematologic and solid tumor cell lines of various origins (e.g. leukemia, lymphoma, breast, colon, uterine), with IC 50 values extending down into the nanomolar range. Cell lines with multi-drug resistant (MDR) phenotypes are similarly sensitive to Rosabulin. The mechanism of action for Rosabulin is inhibition of microtubule assembly and subsequent arrest of the cell cycle. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

When dosed orally or intravenously, Rosabulin (STA 5312) has shown in vivo activity in several murine tumors as well as human tumor xenograft models, including drug resistant tumors . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

3-[(4-Cyanophenyl)methyl]-N-(3-methyl-5-isothiazolyl)-alpha-oxo-1-indolizineacetamide | 1-Indolizineacetamide, 3-((4-cyanophenyl)methyl)-N-(3-methyl-5-isothiazolyl)-alpha-oxo- | 2-[3-[(4-cyanophenyl)methyl]indolizin-1-yl]-N-(3-methyl-1, 2-thiazol-5-yl)-2-o

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Rosabulin (STA 5312) is a potent microtubule inhibitor that inhibits microtubule assembly. Rosabulin has broad-spectrum anti-tumor activity.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=NSC(=C1)NC(=O)C(=O)C2=C3C=CC=CN3C(=C2)CC4=CC=C(C=C4)C#N
• IUPAC Name: 2-[3-[(4-cyanophenyl)methyl]indolizin-1-yl]-N-(3-methyl-1,2-thiazol-5-yl)-2-oxoacetamide
• InChIKey: IZZYUABKZYIINT-UHFFFAOYSA-N
• INCHI: 1S/C22H16N4O2S/c1-14-10-20(29-25-14)24-22(28)21(27)18-12-17(26-9-3-2-4-19(18)26)11-15-5-7-16(13-23)8-6-15/h2-10,12H,11H2,1H3,(H,24,28)
• Isomeric SMILES: CC1=NSC(=C1)NC(=O)C(=O)C2=C3C=CC=CN3C(=C2)CC4=CC=C(C=C4)C#N
• Alternate CAS: 501948-05-6
• PubChem CID: 9843935
• Molecular Weight: 400.45

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolopyridines
      • Subclass Indolizines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolopyridines
• Subclass: Indolizines
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolizines
• Alternative Parents: N-arylamides Benzonitriles Aryl ketones Substituted pyrroles Pyridines and derivatives Vinylogous amides Thiazoles Heteroaromatic compounds Secondary carboxylic acid amides Nitriles Azacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indolizine - Benzonitrile - N-arylamide - Aryl ketone - Monocyclic benzene moiety - Pyridine - Substituted pyrrole - Benzenoid - Azole - Pyrrole - Thiazole - Heteroaromatic compound - Vinylogous amide - Secondary carboxylic acid amide - Ketone - Carboxamide group - Nitrile - Carbonitrile - Carboxylic acid derivative - Azacycle - Organic oxide - Organooxygen compound - Organonitrogen compound - Cyanide - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolizines. These are polycyclic compounds containing an indolizine moiety, which is characterized by the presence of a pyrrole ring fused to a pyridine(Pyrrolo[1,2-a]pyridine).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

DU-145 (51482 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HL-60 (67320 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 50 mg/mL (124.86 mM; Need ultrasonic)
• Molecular Weight: 400.500 g/mol
• XLogP3: 4.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 400.099 Da
• Monoisotopic Mass: 400.099 Da
• Topological Polar Surface Area: 116.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 669.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1