Rita

Base Information

• Chemical Name: Rita
• CAS No.: 213261-59-7
• Molecular Formula: C₁₄H₁₂O₃S₂
• Molecular Weight: 292.379
• Hs Code.: 29321900
• NSC Number: 652287
• DSSTox Substance ID: DTXSID40327405
• Nikkaji Number: J1.124.833K
• Wikidata: Q27166742
• ChEMBL ID: CHEMBL1555354
• Mol file: 213261-59-7.mol

Synonyms:2,5-bis(5-hydroxymethyl-2-thienyl)furan;5,5'-(2,5-furandiyl)bis-2-thiophenemethanol;NSC 652287;RITA compound;small molecule RITA

Chemical Property of Rita

Chemical Property:

• Vapor Pressure: 1.92E-09mmHg at 25°C
• Melting Point: 160 °C
• Boiling Point: 464.9°Cat760mmHg
• PKA: 13.43±0.10(Predicted)
• Flash Point: 235°C
• PSA: 110.08000
• Density: 1.396g/cm³
• LogP: 3.72120
• Storage Temp.: Store at -20°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in DMSO (up to 20 mg/ml)
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 292.02278659
• Heavy Atom Count: 19
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

RITA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)C2=CC=C(O2)C3=CC=C(S3)CO)CO
• Description: RITA (reactivation of p53 and induction of tumor cell apoptosis, 213261-59-7) binds to p53 (Kd = 1.5 nM), changing its conformation, preventing it from binding to HDM2 and preventing its proteasomal degradation.1 It also weakly (computed Kd = 22 μM) binds HDM2 in the cleft that contacts the p53 transactivation domain.2 Its restoration of mutant p53 function depends on eIF2α phosphorylation, and it induces apoptosis via p53-dependent and -independent (JNK/SAPK/p38; protein translation) pathways.3-5 Induces senescence in head and neck cancer cells.6
• Uses: NSC 652287, a DNA damaging agent. It induces p53 tumor suppressor protein. A cell-permeable, p53-targeting, tricyclic thiophene derivative

Technology Process of Rita

There total 6 articles about Rita 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: 98.0%

C14H10O3S2 (443095-23-6) → RITA (213261-59-7)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 0.5h; Cooling with ice;

DOI:10.1039/c2ob26627j

Reference yield: 55.0%

C14H10O2S2 → RITA (213261-59-7)

Guidance literature:

With water; potassium hydroxide; In dimethyl sulfoxide; at 80 ℃; for 4h; Green chemistry;

DOI:10.1016/j.tetlet.2014.10.074

Reference yield:

5-(5-bromofuran-2-yl)thiophene-2-carbaldehyde (1375927-88-0) → RITA (213261-59-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol; dichloromethane / 0.5 h / Cooling with ice

2: XPhos; potassium carbonate; palladium diacetate / acetonitrile; water / 24 h / 20 °C / Inert atmosphere

3: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.5 h / Cooling with ice

With sodium tetrahydroborate; palladium diacetate; potassium carbonate; XPhos; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 2: |Suzuki Coupling;

DOI:10.1039/c2ob26627j

upstream raw materials:

5-(5-bromofuran-2-yl)thiophene-2-carbaldehyde

(5-(5-bromofuran-2-yl)thiophen-2-yl)methanol

C₁₄H₁₀O₃S₂

5-bromo-2-thiophencarboxaldehyde

Refernces

• 1、 Lin, Jinshun,Jin, Xiuli,Bu, Yiwen,Cao, Deliang,Zhang, Nannan,Li, Shangfu,Sun, Qinsheng,Tan, Chunyan,Gao, Chunmei,Jiang, Yuyang. "Efficient synthesis of RITA and its analogues: Derivation of analogues with improved antiproliferative activity via modulation of p53/miR-34a pathway". . p. 9734 - 9746. Retrieved 2013/01/16.