Idelalisib

Base Information

• Chemical Name: Idelalisib
• CAS No.: 870281-82-6
• Molecular Formula: C22H18FN7O
• Molecular Weight: 415.43
• Hs Code.: 29399990
• European Community (EC) Number: 807-438-9
• UNII: YG57I8T5M0
• ChEMBL ID: CHEMBL2216870
• DSSTox Substance ID: DTXSID701007266
• Metabolomics Workbench ID: 152112
• NCI Thesaurus Code: C78825
• Nikkaji Number: J3.231.674C
• Pharos Ligand ID: SRSHJAP7DWPW,SRSZU2MKMCYA
• RXCUI: 1544460
• Wikidata: Q5908266
• Wikipedia: Idelalisib
• Mol file: 870281-82-6.mol

Synonyms:CAL 101;CAL-101;CAL101;GS-1101;idelalisib;Zydelig

Chemical Property of Idelalisib

Chemical Property:

• Melting Point: 250-252oC
• Boiling Point: 733.4±70.0 °C(Predicted)
• PKA: 10.00±0.10(Predicted)
• PSA: 101.38000
• Density: 1.47
• LogP: 3.82730
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (>25 mg/ml)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 415.15568639
• Heavy Atom Count: 31
• Complexity: 685

Purity/Quality:

CAL-101 ^*data from reagent suppliers

Safty Information:

• Safety Statements: V

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CCC(C1=NC2=C(C(=CC=C2)F)C(=O)N1C3=CC=CC=C3)NC4=NC=NC5=C4NC=N5
• Isomeric SMILES: CC[C@@H](C1=NC2=C(C(=CC=C2)F)C(=O)N1C3=CC=CC=C3)NC4=NC=NC5=C4NC=N5
• Recent ClinicalTrials: Serial Measurements of Molecular and Architectural Responses to Therapy (SMMART) PRIME Trial
• Recent EU Clinical Trials: A Phase 2 Randomized Study of Loncastuximab Tesirine Versus Idelalisib in Patients with Relapsed or Refractory Follicular Lymphoma (LOTIS 6)
• Recent NIPH Clinical Trials: A Phase 3 Study of LOXO-305 in Chronic Lymphocytic Leukemia/Small Lymphocytic Lymphoma
• Description: Idelalisib (CAS 870281-82-6) is a potent (IC50 = 2.5nM) and selective (IC50’s: PI3Ka = 820nM, PI3Kb = 565nM, PI3Kg = 89nM) PI3Kd inhibitor.1,2 Useful clinical agent for the treatment of various blood cancers. Idelalisib attenuates regulatory T cells (Treg) but not conventional T cells (Tconv) resulting in a significant increase in tumor-infiltrating antigen-specific CD8 T cells in a murine lung cancer model.3 Conversely, systemic PI3Kd inactivation antagonized anti-CTLA-4 and anti-PD-L1 treatment.4 Others have found that Idelalisib minimally influenced rituximab- and obinutuzumab-mediated Ab-dependent cellular cytotoxicity in human lymphoma cells.5
• Uses: CAL-101 is a PI3K/mTOR pathway inhibitor used in the treatment of myeloid leukemia through sensitizing the cells to combatting drugs. Potent PI3K-p110-delta inhibitor.

Technology Process of Idelalisib

There total 29 articles about Idelalisib 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: 88.0%

C27H28FN7O4 → 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]-3,4-dihydroquinazolin-4-one (870281-82-6)

Guidance literature:

With iodine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at 30 ℃; for 6h; Solvent; Temperature;

Reference yield: 60.0%

2-{[(2S)-2-amino(7H-purin)butanoyl]amino}-6-fluoro-N-phenylbenzamide → 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]-3,4-dihydroquinazolin-4-one (870281-82-6)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; In acetonitrile; for 4h; Reagent/catalyst; Solvent; Reflux;

DOI:10.1039/c8ra00407b

Reference yield:

(S)-2-(1-((9H-purin-6-yl-2,8-d2)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one (870281-86-0) + 6-chloro-7H-purine (87-42-3,111055-92-6) → 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]-3,4-dihydroquinazolin-4-one (870281-82-6)

Guidance literature:

With triethylamine; In tert-butyl alcohol; at 30 - 85 ℃; for 24h; Concentration; Reagent/catalyst;

upstream raw materials:

aniline

9-(triphenylmethyl)adenine

adenine

di-tert-butyl (9-trityl-9H-purin-6-yl)-di-carbamate

Refernces

• 1、 Boggu, Pulla Reddy,Cheon, Min Gyeong,Jung, Young Hoon,Kim, Gahee,Kim, Jong Woo,Kim, Yeon Su,Koh, Su Youn,Lee, Chi Woo,Park, Gi Min,Park, Seo Hyun,Park, Sung Lyea. "Synthesis and biological evaluation of novel purinyl quinazolinone derivatives as PI3Kδ-specific inhibitors for the treatment of hematologic malignancies". . . Retrieved 2021/08/04.
• 2、 -. "Preparation method of Idelalisib". . . Retrieved 2017/04/11.