ChemicalBook > CAS DataBase List > 4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID

4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID

Product Name: 4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID
CAS No.: 155877-83-1
Chemical Name: 4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID
Synonyms: LE 135;LE135, 10 mM in DMSO;4-(7,8,9,10-Tetrahydro-5,7,7,10,10-pentamethyl-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid;4-(5,7,7,10,10-Pentamethyl-7,8,9,10-tetrahydro-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid;4-(7,8,9,10-Tetrahydro-5,7,7,10,10-pentamethyl-(5H)-benzo[e]naphtho[2.3-b][1.4]diazepine-13-yl)benzoicacid;Benzoic acid, 4-(7,8,9,10-tetrahydro-5,7,7,10,10-pentaMethyl-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)-
CBNumber: CB8162724
Molecular Formula: C29H30N2O2
Formula Weight: 438.56
MOL File: 155877-83-1.mol

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4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID Property

Boiling point:: 601.3±55.0 °C(Predicted)
Density: 1.17±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: soluble15mg/mL, clear
pka: 3.02±0.10(Predicted)
form: powder
color: yellow to orange

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Safety

Hazard Codes: Xi
Risk Statements: 36/38
Safety Statements: 26
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0809
Product name: LE 135
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $103
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML0809
Product name: LE 135
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $418
Updated: 2025/07/31

Cayman Chemical

Product number: 14415
Product name: LE 135
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 14415
Product name: LE 135
Purity: ≥98%
Packaging: 5mg
Price: $100
Updated: 2024/03/01

Cayman Chemical

Product number: 14415
Product name: LE 135
Purity: ≥98%
Packaging: 10mg
Price: $139
Updated: 2024/03/01

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4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID Chemical Properties,Usage,Production

Description

LE 135 is a retinoic acid receptor (RAR) antagonist that displays moderate selectivity for RARβ over RARα (K_is = 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.

Definition

ChEBI: 4-(5,7,7,10,10-pentamethyl-8,9-dihydronaphtho[2,3-b][1,4]benzodiazepin-13-yl)benzoic acid is a dibenzodiazepine.

Biological Activity

Retinoic acid antagonist; displays moderate selectivity for RAR β over RAR α (Ki values are 0.22 and 1.4 μ M respectively). Highly selective over RAR γ and RXR α . Inhibits human HL-60 leukemia cell differentiation induced by Am80 (IC 50 = 150 nM).

Biochem/physiol Actions

LE135 is a retinoic acid receptor (RAR) antagonist with selectivity for RARβ (Ki = 220 nM) over RARα (Ki = 1.4 μM). LE135 inhibits retinoic acid-induced transcriptional activation of RARβ (>70% inhibition at 10 μM), but not RARα, RARγ or retinoid X receptor α (RXRα). There is high interest in retinoic acid receptors for cancer and for differentiation studies. LE135 has been shown to inhibit retinoid Am80-induced differentiation of human promyelocytic leukemia HL-60 cells with an IC50 value of 0.2 μM. LE135 has been used to study the role of a retinoic acid receptor-β (RARβ) on the differentiation of mesenchymal stem cells, and was found to inhibit the neuronal differentiation promoting effects of all-trans retinoic acid (ATRA) on mesenchymal stem cells.

storage

Store at +4°C

References

[1] Y LI. Identification of a novel class of retinoic acid receptor beta-selective retinoid antagonists and their inhibitory effects on AP-1 activity and retinoic acid-induced apoptosis in human breast cancer cells.[J]. The Journal of Biological Chemistry, 1999, 274 22: 15360-15366. DOI: 10.1074/jbc.274.22.15360
[2] LAURENCE EYROLLES. Retinobenzoic Acids. 6. Retinoid Antagonists with a Heterocyclic Ring[J]. Journal of Medicinal Chemistry, 1994, 37 10: 1508-1517. DOI: 10.1021/jm00036a017
[3] HIROKI UMEMIYA. Regulation of Retinoidal Actions by Diazepinylbenzoic Acids. 1 Retinoid Synergists Which Activate the RXR?RAR Heterodimers[J]. Journal of Medicinal Chemistry, 1997, 40 26: 4222-4234. DOI: 10.1021/jm9704309

4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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155877-83-1, 4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACIDRelated Search:

3,4-BIS(1-METHYLETHYL)-BENZENAMINE 4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID P-METHYLBENZYLIDENE-P-BUTYLANILINE (4-TERT-BUTYL-PHENYL)-PHENYL-AMINE 4-Ethyl-3-(1-methylethyl)benzenamine LE 540 4-(TERT-BUTYL)-1,2-DIAMINOBENZENE

LE 135

4-(7,8,9,10-Tetrahydro-5,7,7,10,10-pentamethyl-(5H)-benzo[e]naphtho[2.3-b][1.4]diazepine-13-yl)benzoicacid

Benzoic acid, 4-(7,8,9,10-tetrahydro-5,7,7,10,10-pentaMethyl-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)-

4-(5,7,7,10,10-Pentamethyl-7,8,9,10-tetrahydro-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid

4-(7,8,9,10-Tetrahydro-5,7,7,10,10-pentamethyl-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid

LE135, 10 mM in DMSO

155877-83-1

Intracellular receptor