4-(5,6-Dihydro-5,5-dimethyl-8-(quinolin-3-yl)naphthalen-2-carboxamido)benzoic acid
Basic information
- CAS
182135-66-6- Standard SMILES
CC1(C)CC=C(c2cnc3ccccc3c2)c2cc(C(=O)Nc3ccc(C(=O)O)cc3)ccc21- InChIKey
WGLMBRZXZDAQHP-UHFFFAOYSA-N- Molecular formula
- C29H24N2O3
- Average molar mass
- 448.5 g/mol
- Monoisotopic mass
- 448.17869263
Overview
BMS 195614 is a carboxamide resulting from the formal condensation of the carboxy group of 5,5-dimethyl-8-(quinolin-3-yl)-5,6-dihydronaphthalene-2-carboxylic acid with the amino group of p-aminobenzoic acid. It is a neutral retinoic acid receptor (RAR) alpha-selective antagonist (Ki = 2.5 nM). It displays no significant effect on nuclear receptor corepressor (NCoR) binding; moderately decreases SMRT binding to RAR. It antagonizes agonist-induced coactivator (CoA) recruitment. It has a role as a retinoic acid receptor alpha antagonist. It is a secondary carboxamide, a member of benzoic acids and a member of quinolines.
Names & identifiers
- Preferred name
- 4-(5,6-Dihydro-5,5-dimethyl-8-(quinolin-3-yl)naphthalen-2-carboxamido)benzoic acid
- IUPAC
- 4-[(5,5-dimethyl-8-quinolin-3-yl-6H-naphthalene-2-carbonyl)amino]benzoic acid
- English name
- BMS 195614
- Molecular formula
- C29H24N2O3
- Molecular weight
- 448.51
Names & synonyms
RefChem:9122044-(5,6-dihydro-5,5-dimethyl-8-(quinolin-3-yl)naphthalen-2-carboxamido)benzoic acidBMS 195614182135-66-6253310-42-8BMS-195614BMS614BMS-6144-[(5,5-dimethyl-8-quinolin-3-yl-6H-naphthalene-2-carbonyl)amino]benzoic acid4-[[[5,6-dihydro-5,5-dimethyl-8-(3-quinolinyl)-2-naphthalenyl]carbonyl]amino]benzoic acidBMS 6144-[(5,5-dimethyl-8-quinolin-3-yl6H-naphthalene-2-carbonyl)amino]benzoic acid
Show more names
BMS195614,BMS 195614BMS-195614 >=97% (HPLC)WGLMBRZXZDAQHP-UHFFFAOYSA-N4-(5,5-Dimethyl-8-(quinolin-3-yl)-5,6-dihydronaphthalene-2-carboxamido)benzoic acidBenzoic acid, 4-[[[5,6-dihydro-5,5-dimethyl-8-(3-quinolinyl)-2-naphthalenyl]carbonyl]amino]-
BMS195614CID:445091GTPL2643orb1704871orb1785921SCHEMBL6756065CHEMBL2385269SCHEMBL38698427
Properties
Computed structural properties
- XLogP
- 5.7
- Topological polar surface area
- 79.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 797
Physicochemical properties
- Boiling point
- 607.3 · 607.3±55.0 °C(Predicted)
- Density
- 1.285 · 1.285±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
- form
- A crystalline solid
- pka
- 4.27 · 4.27±0.10(Predicted)
- color
- White to off-white
- InChIKey
- WGLMBRZXZDAQHP-UHFFFAOYSA-N
- SMILES
- CC1(C)CC=C(C2=CN=C(C=CC=C3)C3=C2)C4=C1C=CC(C(NC5=CC=C(C(O)=O)C=C5)=O)=C4
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionBMS614 is a neutral retinoic acid receptor (RAR) α-selective antagonist (Ki = 2.5 nM). BMS614 antagonizes agonist-induced coactivator (CoA) recruitment.
UsesBMS-195614 (BMS 614) is an orally active neutral RARα-selective antagonist with a Ki of 2.5 nM. BMS-195614 restores the expression of Bcl2. BMS-195614 inhibits the transactivation of NF-κB, AP-1 and PPAR. BMS-195614 downregulates the expression of IL-6 and VEGF. BMS-195614 reduces blue light-induced phototoxicity and inhibits cell migration. BMS-195614 modulates inflammation and angiogenesis[1][2][3][4][5].
Additional notes
DefinitionChEBI: BMS 195614 is a carboxamide resulting from the formal condensation of the carboxy group of 5,5-dimethyl-8-(quinolin-3-yl)-5,6-dihydronaphthalene-2-carboxylic acid with the amino group of p-aminobenzoic acid. It is a neutral retinoic acid receptor (RAR) alpha-selective antagonist (Ki = 2.5 nM). It displays no significant effect on nuclear receptor corepressor (NCoR) binding; moderately decreases SMRT binding to RAR. It antagonizes agonist-induced coactivator (CoA) recruitment. It has a role as a retinoic acid receptor alpha antagonist. It is a member of quinolines, a member of benzoic acids and a secondary carboxamide.
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