Indirubin-3'-monoxime

Base Information

• Chemical Name: Indirubin-3'-monoxime
• CAS No.: 160807-49-8
• Molecular Formula: C₁₆H₁₁N₃O₂
• Molecular Weight: 277.282
• Hs Code.: 2933990090
• NSC Number: 717829
• DSSTox Substance ID: DTXSID90416111
• Nikkaji Number: J2.522.312H,J741.372F
• Wikidata: Q27078054,Q27461594
• Pharos Ligand ID: 4Q3USMQH98XS
• ChEMBL ID: CHEMBL216543,CHEMBL126077,CHEMBL1496098
• Mol file: 160807-49-8.mol

Synonyms:indirubin 3'-oxime;indirubin-3'-monoxime

Chemical Property of Indirubin-3'-monoxime

Chemical Property:

• Appearance/Colour: Dark Red Solid
• Melting Point: 247-249°C
• Boiling Point: 532.2±50.0 °C(Predicted)
• PKA: 8.66±0.20(Predicted)
• PSA: 73.72000
• Density: 1.50
• LogP: 2.92980
• Storage Temp.: Store at RT
• Solubility.: DMSO: >10 mg/mL
• Water Solubility.: DMSO: >10 mg/mL
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 277.085126602
• Heavy Atom Count: 21
• Complexity: 405

Purity/Quality:

99% ^*data from raw suppliers

Indirubin-3?-monoxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)O)C3=C(C4=CC=CC=C4N3)N=O
• Description: Indirubin-3’-oxime is a potent inhibitor of glycogen synthase kinase 3β (GSK3β; IC50 = 22 nM). As GSK3β phosphorylates tau protein, indirubin-3’-oxime prevents tau phosphorylation both in vitro and in vivo at Alzheimer’s disease-relevant sites. It also inhibits cyclin-dependent kinases (CDKs) at higher concentrations, including Cdk1/cyclin B (IC50 = 180 nM), Cdk2/cyclin A (IC50 ~500 nM), Cdk2/cyclin E (IC50 = 250nM), Cdk4/cyclin D1 (IC50 = 3.3 μM) and Cdk5/p35 (IC50 = 100 nM). Indirubin-3’-oxime reversibly inhibits the proliferation of many cells types, arresting cycling in the G2/M phase.
• Uses: A potent inhibitor of GSK-3? (IC50=22nM). Also inhibits CDK1 (IC50=180nM) and CDK (IC50=100nM). It reversibly arrests asynchronous HBL-100 cells at G2. It induces apoptosis in the mammary carcinoma cell line MCF-7 (10üM). Indirubin-3′-oxime has been used in the inhibition of glycogen synthase kinase 3 in human monocytic cell line, THP-1.

Technology Process of Indirubin-3'-monoxime

There total 22 articles about Indirubin-3'-monoxime 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%

indirubin (479-41-4) → indirubin-3'-monoxime (667463-82-3,160807-49-8)

Guidance literature:

With potassium hydroxide; hydroxylamine hydrochloride; In ethanol; for 2h; Heating;

DOI:10.1246/bcsj.69.1621

Reference yield: 93.0%

3-indoxyl acetate (608-08-2) + indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → indirubin-3'-oxime (160807-49-8)

Guidance literature:

With sodium carbonate; In methanol; at 20 ℃; for 3h; Inert atmosphere;

Reference yield: 93.0%

indirubin (479-41-4) → indirubin-3'-oxime (160807-49-8)

Guidance literature:

With pyridine; hydroxylamine hydrochloride; at 120 ℃; for 5h;

DOI:10.1080/14786410802300469

upstream raw materials:

indirubin

indole-2,3-dione

(2R)-2-(acetyloxy)-4-({[(2Z,3E)-2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,2-dihydro-3H-indol-3-ylidene]amino}oxy)-N,N,N-trimethyl-4-oxobutan-1-aminium chloride

3-indoxyl acetate

Downstream raw materials:

indirubin-3′-(3,4-dihydroxybutyl)oxime ether

Refernces

• 1、 Evdokimov, Nikolai M.,Magedov, Igor V.,McBrayer, Dominic,Kornienko, Alexander. "Isatin derivatives with activity against apoptosis-resistant cancer cells". . p. 1558 - 1560. Retrieved 2016.
• 2、 Kosuge, Yasuhiro,Saito, Hiroaki,Haraguchi, Tatsuki,Ichimaru, Yoshimi,Ohashi, Sachiyo,Miyagishi, Hiroko,Kobayashi, Shunsuke,Ishige, Kumiko,Miyairi, Shinichi,Ito, Yoshihisa. "Indirubin derivatives protect against endoplasmic reticulum stress-induced cytotoxicity and down-regulate CHOP levels in HT22 cells". . p. 5122 - 5125. Retrieved 2017.
• 3、 Nguyen, Dan Trong,Truong, Giang Nguyen,Van Vuong, Truong,Van, Tai Nguyen,Manh, Cuong Nguyen,Dao, Cuong To,Thuy, Thuy Dinh Thi,Van, Chinh Luu,Khac, Vu Tran. "Synthesis of new indirubin derivatives and their in vitro anticancer activity". . p. 1083 - 1092. Retrieved 2019.
• 4、 Lee, Sung-Bau,Chang, Ting-Yu,Lee, Nian-Zhe,Yu, Zih-Yao,Liu, Chi-Yuan,Lee, Hsueh-Yun. "Design, synthesis and biological evaluation of bisindole derivatives as anticancer agents against Tousled-like kinases". . . Retrieved 2021/10/20.
• 5、 An, Jianxiong,Cao, Zhuoxian,Gu, Zhicheng,He, Bin,Li, Yan,Li, Yongjun,Lin, Hening,Lin, Shuxian,Liu, Ting,Wang, Jie,Wang, Pan,Yang, Fenfen,Zhao, Yonglong. "Indirubin Derivatives as Dual Inhibitors Targeting Cyclin-Dependent Kinase and Histone Deacetylase for Treating Cancer". . p. 15280 - 15296. Retrieved 2021/10/25.