4-(5,7,7,10,10-Pentamethyl-8,9-dihydronaphtho[2,3-b][1,4]benzodiazepin-13-yl)benzoic acid

Base Information

• Chemical Name: 4-(5,7,7,10,10-Pentamethyl-8,9-dihydronaphtho[2,3-b][1,4]benzodiazepin-13-yl)benzoic acid
• CAS No.: 155877-83-1
• Molecular Formula: C₂₉H₃₀N₂O₂
• Molecular Weight: 438.569
• European Community (EC) Number: 806-164-7
• DSSTox Substance ID: DTXSID70439469
• Nikkaji Number: J588.743G
• Wikidata: Q27079800
• ChEMBL ID: CHEMBL37708
• Mol file: 155877-83-1.mol

Synonyms:4-(5H-7,8,9,10-tetrahydro-5,7,7,10,10-pentamethylbenzo(e)naphtho(2,3-b)(1,4)diazepin-13-yl)benzoic acid;LE 135;LE-135;LE135

Chemical Property of 4-(5,7,7,10,10-Pentamethyl-8,9-dihydronaphtho[2,3-b][1,4]benzodiazepin-13-yl)benzoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.628
• Boiling Point: 601.336°C at 760 mmHg
• PKA: 3.02±0.10(Predicted)
• Flash Point: 317.477°C
• PSA: 52.90000
• Density: 1.176g/cm³
• LogP: 6.48480
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: soluble15mg/mL, clear
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 438.230728204
• Heavy Atom Count: 33
• Complexity: 779

Purity/Quality:

98%,99%, ^*data from raw suppliers

LE 135 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(C2=CC3=C(C=C21)N=C(C4=CC=CC=C4N3C)C5=CC=C(C=C5)C(=O)O)(C)C)C
• Description: LE 135 is a retinoic acid receptor (RAR) antagonist that displays moderate selectivity for RARβ over RARα (Kis = 0.22 and 1.4 μM, respectively). LE 135 inhibits retinoic acid-induced transcriptional activation of RARβ (>70% inhibition at 10 μM), but not RARα, RARγ or retinoid X receptor α. It has been shown to inhibit retinoid Am80-induced differentiation of human promyelocytic leukemia cells, HL-60, with an IC50 value of 0.2 μM.
• Uses: LE 135 has been used for in vitro islet treatment.

Technology Process of 4-(5,7,7,10,10-Pentamethyl-8,9-dihydronaphtho[2,3-b][1,4]benzodiazepin-13-yl)benzoic acid

There total 11 articles about 4-(5,7,7,10,10-Pentamethyl-8,9-dihydronaphtho[2,3-b][1,4]benzodiazepin-13-yl)benzoic acid 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:

4-(5,7,7,10,10-Pentamethyl-7,8,9,10-tetrahydro-5H-5,12-diaza-benzo[4,5]cyclohepta[1,2-b]naphthalen-13-yl)-benzoic acid methyl ester (155877-82-0) → LE135 (155877-83-1)

Guidance literature:

With sodium hydroxide; In ethanol; for 2h;

DOI:10.1021/jm00036a017

Reference yield:

bromobenzene (108-86-1,52753-63-6) → LE135 (155877-83-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 48 percent / K₂CO₃, CuI / 12 h / 180 °C

2: 1.) NaH / 1.) DMF, 20 min, 2.) DMF, 20 min

3: 53 percent / Fe, aq. HCl / ethanol / 1 h / Heating

4: 83 percent / pyridine / benzene / 1 h

5: 66 percent / polyphosphoric acid / 0.5 h / 140 °C

6: 2 N aq. NaOH / ethanol / 2 h

With pyridine; hydrogenchloride; sodium hydroxide; copper(l) iodide; PPA; iron; sodium hydride; potassium carbonate; In ethanol; benzene;

DOI:10.1021/jm00036a017

Reference yield:

2,5-dichloro-2,5-dimethyl hexane (6223-78-5) → LE135 (155877-83-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 55 percent / AlCl₃ / CH₂Cl₂ / 0.33 h / 0 °C

2: 52 percent / KNO₃, trifluoromethanesulfonic acid / 1.5 h / Ambient temperature

3: 99 percent / 2 N aq. NaOH / ethanol / 2 h / Heating

4: 48 percent / K₂CO₃, CuI / 12 h / 180 °C

5: 1.) NaH / 1.) DMF, 20 min, 2.) DMF, 20 min

6: 53 percent / Fe, aq. HCl / ethanol / 1 h / Heating

7: 83 percent / pyridine / benzene / 1 h

8: 66 percent / polyphosphoric acid / 0.5 h / 140 °C

9: 2 N aq. NaOH / ethanol / 2 h

With pyridine; hydrogenchloride; sodium hydroxide; copper(l) iodide; aluminium trichloride; PPA; trifluorormethanesulfonic acid; iron; sodium hydride; potassium carbonate; potassium nitrate; In ethanol; dichloromethane; benzene;

DOI:10.1021/jm00036a017

upstream raw materials:

4-(5,7,7,10,10-Pentamethyl-7,8,9,10-tetrahydro-5H-5,12-diaza-benzo[4,5]cyclohepta[1,2-b]naphthalen-13-yl)-benzoic acid methyl ester

bromobenzene

2,5-dichloro-2,5-dimethyl hexane

Acetanilid

Refernces