1600-81-3

Basic information

• Product Name: 10a,12a-dimethyl-1,3,4,4a,4b,5,6,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-2,8-dione
• Synonyms: CHAND-004
• CAS NO: 1600-81-3
• Molecular Formula: C₁₉H₂₇NO₂
• Molecular Weight: 301.4232
• Mol File: 1600-81-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 501.3°C at 760 mmHg
• Flash Point: 177.6°C
• Density: 1.14g/cm³
• Vapor Pressure: 3.51E-10mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 10a,12a-dimethyl-1,3,4,4a,4b,5,6,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-2,8-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 10a,12a-dimethyl-1,3,4,4a,4b,5,6,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-2,8-dione(1600-81-3)
• EPA Substance Registry System: 10a,12a-dimethyl-1,3,4,4a,4b,5,6,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-2,8-dione(1600-81-3)

Safety Data

• Hazardous Substances Data: 1600-81-3(Hazardous Substances Data)

Usage

Molecular structure

A complex structure consisting of a naphthalene and quinoline fused together, with a total of 14 carbon atoms and multiple methyl groups.

Classification

A synthetic derivative of naphthalene and quinoline, classified as a quinoline alkaloid.

Potential applications

May have potential applications in medicinal chemistry due to its structural features that are common among natural products with promising biological activities.

Biological activity

Its precise biological activities are not well-documented, but it may exhibit properties similar to other quinoline alkaloids.

Hazards

The potential hazards of this compound are not well-documented, and further research may be needed to fully understand its characteristics and potential risks.

Research status

Further research is needed to fully understand its properties, uses, and potential applications.

Synonyms

Also known as dodecahydro-10,12-dimethyl-1,3,6-(epiminomethylene) phenanthro[5,4,3-cde]indole-2,8-dione.

Molecular weight

Approximately 335.43 g/mol

Appearance

The appearance of this compound is not well-documented, but it is likely a solid due to its molecular weight and complexity.

Solubility

The solubility of this compound is not well-documented, but it may be soluble in organic solvents such as ethanol or methanol.

Stability

The stability of this compound is not well-documented, but it may be sensitive to heat, light, or moisture, as is common with many organic compounds.

Synthesis

The synthesis of this compound likely involves the fusion of naphthalene and quinoline rings, followed by the addition of methyl groups and other functional groups.

Structural features

This compound has a complex structure with multiple fused rings, multiple methyl groups, and a carbonyl group at the 2 and 8 positions.

Potential for further research

Due to its complex structure and potential applications in medicinal chemistry, this compound may be a valuable target for further research and development.

Upstream product

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Downstream Products

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Relevant articles and documents

Hemisynthesis, computational and molecular docking studies of novel nitrogen containing steroidal aromatase inhibitors: Testolactam and testololactam

Testololactone (10) and testolactone (11) represent aromatase inhibitors containing lactone rings. We previously reported their hemisynthesis from the most common phytosterols, which are highly abundant in nature. Herein, we report the synthesis of their nitrogen congeners: testololactam (3) and testolactam (8). The reaction process involves the conversion of 4-androstene-3,17-dione to its corresponding oxime using hydroxylamine hydrochloride, whose Beckmann rearrangement under acid conditions yielded the desired testololactam (3). However, testolactam (8) was formed by the Beckmann rearrangement of the oxime (7) of 1,4-androstene-3,17-dienone (6). This expeditious reaction scheme may be exploited for the bulk production of testololactam (3) and testolactam (8). Theoretical DFT studies concerning the structural and electronic properties of all the end products were carried out using the Becke three-parameter Lee-Yang-Parr function (B3LYP) and 6-31G(d,p) level of theory. Molecular electrostatic potential map and frontier orbital analysis were carried out. The HOMO-LUMO energy gap was calculated, which allowed the calculation of relative reactivity descriptors like chemical hardness, chemical inertness, chemical potential, nucleophilicity and electrophilicity index of the synthesized products. The molecular docking studies of testololactam (3), testolactam (8) and testololactone (10), with aromatase (CYP19) revealed binding free energies of (ΔGb) = -9.85, -9.62 and -10.14 kcal mol-1 respectively, compared to the standard testolactone (11), a well-known aromatase inhibitor sold under the brand name TESLAC, which exhibited a binding free energy (ΔGb) of -10.29 kcal mol-1 with an inhibition constant Ki of 28.87 nM. The docking study revealed that the nitrogen congeners exhibit a relatively lower but appreciable therapeutic efficiency to be used as aromatase inhibitors.

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Synthesis and biological evaluation of novel unsaturated carboxysteroids as human 5α-reductase inhibitors: A legitimate approach

In the present study, novel steroidal 17a-substituted 3-cyano-17a-aza-D- homo-3,5-androstadien-17-ones (12-19) and 17a-substituted 17-oxo-17a-aza-D-homo- 3,5-androstadien-3-oic acids (20-26) were synthesized from dehydroepiandrosterone acetate (6) along with 17-oxo-19-nor-3,5-androstadien-3- oic acid (30) through a multistep synthesis. Compounds were evaluated for their in vitro 5α-reductase inhibitory activity by measuring the conversion of [3H] androstenedione in human embryonic kidney (HEK) cells. In vivo 5α-reductase inhibitory activity was also determined using rat prostate weighing method. Compounds 21-23 and 25 showed potent inhibition of 5α-reductase II enzyme with IC50 values of 54.1 ± 9.5, 22.1 ± 2.4, 72.8 ± 2.3 and 26.5 ± 4.4 nM respectively as compared to Finasteride (30.3 nM) along with a significant (p 0.05) reduction in rat prostate weight.