116233-17-1

Basic information

• Product Name: 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine
• Synonyms: 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine;3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine
• CAS NO: 116233-17-1
• Molecular Formula: C₁₅H₂₃N
• Molecular Weight: 217.34982
• EINECS: 1806241-263-5
• Mol File: 116233-17-1.mol

Chemical Properties

• Boiling Point: 321.2 °C at 760 mmHg
• Flash Point: 148.8 °C
• Appearance: /
• Density: 0.938 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine(116233-17-1)
• EPA Substance Registry System: 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine(116233-17-1)

Safety Data

• Hazardous Substances Data: 116233-17-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine is used as a reagent in chemical reactions for the manufacturing of various organic compounds. Its unique structure and properties make it a valuable component in the synthesis of a range of products.
Used in Fragrance and Perfume Industry:
In the fragrance and perfume industry, 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine is used as a key ingredient for its aromatic properties. It contributes to the creation of distinct scents and enhances the overall sensory experience of perfumes and fragrances.
Used in Medicinal and Pharmaceutical Fields:
5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenamine is also being studied for its potential applications in the medicinal and pharmaceutical fields. Its unique chemical structure may offer new avenues for the development of pharmaceutical compounds and treatments for various medical conditions.

Upstream product

• 116233-16-0 1,2,3,4-tetrahydro-1,1,4,4,6-pentamethyl-7-nitronaphthalene 
• 6223-78-5 2,5-dichloro-2,5-dimethyl hexane 
• 6683-48-3 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene 
• 110-03-2 2,5-dimethyl-2,5-hexanediol 
• 108-88-3 toluene 

Downstream Products

• 116263-41-3 methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)cerbamoyl>benzoate 
• 214694-11-8 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamino)-benzoic acid ethyl ester 
• 178264-46-5 N-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl)-2-naphthalenyl 4-ethoxycarbonyl benzaldimine 
• 1271910-74-7 N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4-phenylbutanamide 
• 1271910-76-9 4-(3,4-dimethoxyphenyl)-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)butanamide 
• 1271910-80-5 E-3-(3,4-dihydroxyphenyl)-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide 
• 1271910-82-7 E-3-(4-hydroxy-3-methoxyphenyl)-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide 
• 1271910-84-9 E-3-(3,4-dimethoxyphenyl)-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide 
• 1271910-78-1 E-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cinnamamide 
• 1227244-08-7 3-nitro-4-[N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)amino]benzoic acid methyl ester 
• 1416254-96-0 C₂₅H₃₃NO₂ 
• 1416254-97-1 C₂₇H₃₇NO₂ 
• 1416255-01-0 C₂₆H₃₃NO₂ 
• 1416255-02-1 C₂₈H₃₇NO₂ 

Relevant articles and documents

Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR)-Selective Agonists: Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and 6-(Ethyl(5,5,8,8-tetrahydronaphthalen-2-yl)amino)nicotinic Acid (NEt-TMN)

Sulfonic acid analogues of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene, 1) as well as seven novel and two reported analogues of 6-(ethyl(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)nicotinic acid (NEt-TMN) were synthesized and assessed for selective retinoid X receptor (RXR) agonism. Compound 1 is FDA-approved for treatment of cutaneous T-cell lymphoma (CTCL); however, 1 can provoke side effects by impacting RXR-dependent receptor pathways. All of the analogues in this study were evaluated for their potential to bind RXR through modeling and then assayed in an RXR-RXR mammalian-2-hybrid (M2H) system and in RXR-responsive element (RXRE)-mediated transcriptional experiments. The EC50 profiles for these unique analogues and their analogous effectiveness to inhibit proliferation in CTCL cells relative to 1 suggest that these compounds possess similar or even enhanced therapeutic potential. Several compounds also displayed more selective RXR activation with minimal cross-signaling of the retinoic acid receptor. These results suggest that modifications of potent RXR agonists such as NEt-TMN can lead to improved biological selectivity and potency compared with the known therapeutic.

DIHYDROINDENE AND TETRAHYDRONAPHTHALENE COMPOUNDS

The invention provides compounds of formula I: and salts thereof, as well as pharmaceutical compositions comprising such compounds. The compounds are useful for treating cancers, Alzheimer's disease, and conditions associated with demyelination.

THERAPEUTIC COMPOUNDS

The invention provides compounds and compositions that are useful for treating conditions including Alzheimer's disease, Parkinson's disease, diabetes, cancer, and psychotic disorders such as schizophrenia.

Mechanism of retinoid X receptor partial agonistic action of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-1H-benzotriazole-5- carboxylic acid and structural development to increase potency

We have reported that retinoid X receptor (RXR) partial agonist 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-1H-benzotriazole-5- carboxylic acid (CBt-PMN, 4a) shows a significant antidiabetes effect in the KK-Ay type 2 diabetes model

Synthesis and effects of some novel tetrahydronaphthalene derivatives on proliferation and nitric oxide production in lipopolysaccharide activated Raw 264.7 macrophages

In this study, novel N-(3,5,5,8,8-pentamethyl-5,6,7,8- tetrahydronaphthalene-2-yl)-carboxamide (6-15) and 5,5,8,8-tetramethyl-5,6,7,8- tetrahydronaphthalene-2-carboxamide (16-32) derivatives were synthesized and their in vitro effects at 5 μM and 50 μM concentrations on proliferation and nitric oxide (NO) production in lipopolysaccharide (LPS) activated RAW 264.7 macrophage cells were determined. Compounds 12, 17, 24 and 26 were found to decrease nitrite levels in a dose-dependent manner in LPS-activated cells. At the tested concentrations, these compounds did not exhibit cytotoxic effects. Interestingly, compound 27 which contains nitroxide free radical was the most active compound in this series showing 59.2% nitrite inhibition in LPS-activated macrophage cells.

Synthesis and antioxidant activity of new tetrahydro-naphthalene-indole derivatives as retinoid and melatonin analogs

A number of retinoid-related compounds represent classes of antioxidative and proapoptotic agents with promising potential in the treatment of neoplastic diseases. Indeed, the synthetic retinoid amide fenretinide [N-(4-hydroxyphenyl) retinamide] induces apoptosis of cancer cells and acts as a chemotherapeutic drug in cancer therapy. In the present work, and as a continuation of our studies on retinoid-type compounds, the synthesis of melatonin retinamide derivatives was studied as a novel series of melatonin retinoids, using the condensation reaction sequence involving tetrahydrotetramethylnaphthalene carboxylic acid and appropriate melatonin-type moieties. Despite of the weak DPPH inhibition activity pattern of the synthesized compounds, some of them showed a strong inhibition on lipid peroxidation (IVa-b, Va, and VIIa-c, 88, 96, 90, 94, 93, and 86%, respectively at 10-4 M concentration) when melatonin (85% at 10-4 M concentration) was used as a reference compound.

Aza-retinoids as novel retinoid X receptor-specific agonists

A new structurally simple series of potent lipophilic aza-retinoids RXR agonists has been developed. SAR studies for the N-alkyl-azadienoic acids described here demonstrate that the RXR activity profile is sensitive to the N-alkyl chain length. Further, we have expanded the work to include azadienoic acids, which exhibited many accessible conformations leading to a better understanding of the SAR around the series.

Polycyclic heterocyclic compounds, a process for their preparation and their use in human and veterinary medicine

A polycyclic heterocyclic compound has the formula STR1 wherein n is 1 or 2, R1 l represents (i) lower alkyl, (ii) --CH2 OH or (iii) STR2 R2 represents (a) hydrogen, (b) STR3 or (c)--OR3, R3 represents hydrogen, C1 -C20 alkyl mono or polyhydroxyalkyl, aryl or aralkyl optionally substituted, the residue of a sugar or STR4 wherein p is 1, 2, or 3, and r' and r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl optionally substituted, amino acid residue, aminated sugar residue, or together form a heterocycle, X represents oxygen, sulfur, SO, SO2 or --NR4, Y represents CR4 or a nitrogen atom and R4 represents hydrogen or lower alkyl. This polycyclic heterocyclic compound can be used in human and veterinary medicine and especially in the topical or systemic treatment of determatologic diseases.

Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids

A series of conformationally restricted analogues of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propent yl]benzoic acid - (E)-4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphtalenyl)-2-propt enyl]benzoic acid, (E)-4-[3-(5,6,7,8-tet

Retinobenzoic Acids. 1. Structure-Activity Relationships of Aromatic Amides with Retinoidal Activity

Two types of aromatic amides, terephthalic monoanilides and (arylcarboxamido)benzoic acids, have been shown to possess potent retinoidal activities and can be classified as retinoids.The structure-activity relationships of these amides are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60.In generic formula 4 (X = NHCO or CONH), the necessary factors to elicit the retinoidal activities are a medium-sized alkyl group (isopropyl, tert-butyl, etc.) at the meta position and a carboxyl group at the para position of the other benzene ring.The bonding of the amide structure can be reversed, this moiety apparently having the role of locating the two benzene rings at suitable positions with respect to each other.Substitution at the ring position ortho to the amide group or N-methylation of the amido group caused loss of activity, presumably owing to the resultant change of conformation.It is clear that the mutual orientation of the benzylic methyl group(s) and the carboxyl group and their distance apart are essential factors determining the retinoidal activity.Among the synthesized compounds, 4-benzoic acid (Am80) and 4-benzoic acid (Am580) were several times more active than retinoic acid in the assay.They are structurally related to retinoic acid, as is clear from the biological activity of the hybrid compounds (M2 and R2).