OTAVA-BB 7070707015

Base Information

• Chemical Name: OTAVA-BB 7070707015
• CAS No.: 934593-90-5
• Molecular Formula: C26H29NO5
• Molecular Weight: 435.52
• Mol file: 934593-90-5.mol

Synonyms:OTAVA-BB 7070707015;CAY10585;HIF-1α inhibitor;LW6;LW8;4-Hydroxy-3-[[2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)acetyl]aMino]-benzoic Acid Methyl Ester;Hypoxia inducible factor-1α inhibitor

Chemical Property of OTAVA-BB 7070707015

Chemical Property:

• Boiling Point: 647.4±55.0 °C(Predicted)
• PKA: 7.59±0.48(Predicted)
• Density: 1.295±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

4-Hydroxy-3-[[2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)acetyl]amino]-benzoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Hypoxia-inducible factor-1 (HIF-1) is a heterodimeric transcription factor composed of a HIF-1α subunit and HIF-1β subunit. Whereas the HIF-1β subunit is constitutively expressed, the HIF-1α subunit is regulated by cellular oxygen levels and therefore plays an important role in maintaining cellular oxygen homeostasis. Under normoxic conditions, HIF-1α is selectively hydroxylated on proline residues 402 and 577 and targeted for destruction by the ubiquitin-proteasome system. Under hypoxic conditions, HIF-1α accumulates and dimerizes with HIF-1β to promote the transcription of a number of genes involved in angiogenesis, glycolysis, growth factor signaling, tumor invasion, and metastasis. CAY10585 is a novel small molecule inhibitor of HIF-1α accumulation and gene transcriptional activity. In a gene reporter assay using human Hep3B and AGS cell lines, CAY10585 prevented HIF-1 transcriptional activity with IC50 values of 2.6 and 0.7 μM, respectively. It blocks HIF-1α accumulation in Hep3B cells in a concentration and time-dependent manner, with complete inhibition at a concentration of 30 μM within 12 hours. CAY10585 also significantly suppresses transcription of the HIF-1 target genes VEGF and erythropoietin at 10 μM.
• Uses: CAY10585 is a class of hypoxia-inducible factor (HIF-1) responsible for radiation resistance and poor prognosis in cancer therapy.

Technology Process of OTAVA-BB 7070707015

There total 7 articles about OTAVA-BB 7070707015 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: 84.1%

(4-adamantan-1-yl-phenoxy)acetic acid (52804-26-9) + methyl 3-amino-4-hydroxybenzoate (536-25-4) → 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester (934593-90-5)

Guidance literature:

(4-adamantan-1-yl-phenoxy)acetic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 20 ℃; for 1h;

methyl 3-amino-4-hydroxybenzoate; With pyridine; In tetrahydrofuran; at 20 ℃; Further stages.;

DOI:10.1021/jm0610292

Reference yield: 84.1%

methyl 3-amino-4-hydroxybenzoate (536-25-4) → 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester (934593-90-5)

Guidance literature:

(4-adamantan-1-yl-phenoxy)acetic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 20 ℃; for 1h;

methyl 3-amino-4-hydroxybenzoate; With pyridine; In tetrahydrofuran; at 20 ℃;

Reference yield:

4-adamantylphenol (29799-07-3) → 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester (934593-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94.6 percent / potassium carbonate / dimethylformamide / 20 °C

2.1: 61.3 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 20 °C

3.1: oxalyl chloride; DMF / tetrahydrofuran / 1 h / 20 °C

3.2: 84.1 percent / pyridine / tetrahydrofuran / 20 °C

With lithium hydroxide; oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jm0610292

upstream raw materials:

methyl 3-amino-4-hydroxybenzoate

(4-adamantan-1-yl-phenoxy)acetic acid

(4-adamantyl-1-yl-phenoxy) acetic acid ethyl ester

4-adamantylphenol

Downstream raw materials:

AC₁-001

methyl 3-[2-(4-adamantan-1-yl-phenoxy)acetylamino]-4-(2,2-dimethyl-4,15-dioxo-3,8,11-trioxa-5,14-diazahexadecan-16-yloxy)benzoate