21816-08-0

Basic information

• Product Name: 3-Bromoadamantane-1-carboxylic acid
• Synonyms: 3-broMo-adaMantaine-1-carboxylic acid;1-BroMo-3-carboxyadaMantane;1-BroMoadaMantane-3-carboxylic acid;3-Bromotricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid, 1-Bromo-3-carboxyadamantane;3-BroMoadaMantane-1-carboxylic acid;3-Bromoadamantane-1-carboxylic acid 97%;3-ADAMANTANECARBOXYLIC ACID, 1-BROMO-;Tricyclo(3.3.1.1(sup 3,7))decane-1-carboxylic acid, 3-bromo- (9CI)
• CAS NO: 21816-08-0
• Molecular Formula: C₁₁H₁₅BrO₂
• Molecular Weight: 259.14
• Product Categories: Organic Building Blocks;Adamantane derivatives;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis
• Mol File: 21816-08-0.mol

Chemical Properties

• Melting Point: 147 °C
• Boiling Point: 354.2 °C at 760 mmHg
• Flash Point: 168 °C
• Appearance: /
• Density: 1.665 g/cm³
• Vapor Pressure: 5.69E-06mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.35±0.40(Predicted)
• CAS DataBase Reference: 3-Bromoadamantane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromoadamantane-1-carboxylic acid(21816-08-0)
• EPA Substance Registry System: 3-Bromoadamantane-1-carboxylic acid(21816-08-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• RTECS: AU4452500
• HazardClass: IRRITANT
• Hazardous Substances Data: 21816-08-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromoadamantane-1-carboxylic acid is used as a key intermediate in the synthesis of novel adamantyl derivatives. These derivatives have demonstrated potent activity as multidrug resistance (MDR) reversal agents, which are crucial in overcoming the resistance of cancer cells to various chemotherapeutic drugs. By modulating the efflux pumps in cancer cells, these adamantyl derivatives can increase the intracellular accumulation of chemotherapeutic agents, thereby enhancing their efficacy and overcoming drug resistance.
Used in Chemical Synthesis:
3-Bromoadamantane-1-carboxylic acid serves as a versatile building block in the synthesis of various organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structural features and functional groups make it an attractive candidate for the development of new molecules with diverse biological activities and properties.

Purification Methods

Purify the acid by recrystallising it from cyclohexane and/or subliming at 130o/10mm. It is converted to the methyl ester (diazomethane) with m 32o (from pet ether at -10o). [Stetter & Mayer Chem Ber 95 667 1962, Stetter & Wulff Chem Ber 93 1366 1960, Bayal & Lantvoev J Org Chem USSR (Engl Trans) 9 291 1973.]

InChI:InChI=1/C11H15BrO2/c12-11-4-7-1-8(5-11)3-10(2-7,6-11)9(13)14/h7-8H,1-6H2,(H,13,14)/p-1/t7-,8-,10?,11?/m1/s1

Upstream product

• 42711-78-4 3-acetoxyadamantane-1-carboxylic acid 
• 50795-82-9 3-nitroxyadamantane-1-carboxylic acid 
• 42711-75-1 3-hydroxyadamantane-1-carboxylic acid 
• 828-51-3 1-Adamantanecarboxylic acid 

Downstream Products

• 27983-08-0 bromo-3 adamantylcarboxylate de methyle 
• 53263-89-1 1-bromo-3-carboxamidoadamantane 
• 36964-33-7 (3-bromotricyclo[3.3.1.1^3,7]dec-1-yl)methanol 
• 39917-36-7 3-bromo-1-adamantanecarbonyl chloride 
• 42711-75-1 3-hydroxyadamantane-1-carboxylic acid 
• 56531-56-7 3-(4-methoxyphenyl)adamantane-1-carboxylic acid 
• 88358-11-6 3-(4-Fluorophenyl)-1-adamantanecarboxylic acid 
• 88358-12-7 3-(4-Methylthiophenyl)-1-adamantanecarboxylic acid 
• 96962-78-6 3-Fluor-1-adamantancarbonsaeurefluorid 
• 126164-71-4 3-(4-hydroxy-2-methylphenyl)adamantanecarboxylic acid 
• 56531-57-8 3-(3,4-Dimethyl-phenyl)-adamantane-1-carboxylic acid 
• 56531-69-2 3-p-Tolyl-adamantane-1-carboxylic acid 
• 768-90-1 1-Adamantyl bromide 
• 281-23-2 adamantane 

Relevant articles and documents

Investigation of the gas phase reactivity of the 1-adamantyl radical using a distonic radical anion approach

The gas phase reactions of the bridgehead 3-carboxylato-1-adamantyl radical anion were observed with a series of neutral reagents using a modified electrospray ionisation linear ion trap mass spectrometer. This distonic radical anion was observed to undergo processes suggestive of radical reactivity including radical-radical combination reactions, substitution reactions and addition to carbon-carbon double bonds. The rate constants for reactions of the 3-carboxylato-1-adamantyl radical anion with the following reagents were measured (in units 10-12 cm3 molecule-1 s -1): 18O2 (85 ± 4), NO (38.4 ± 0.4), I2 (50 ± 50), Br2 (8 ± 2), CH 3SSCH3 (12 ± 2), styrene (1.20 ± 0.03), CHCl3 (H abstraction 0.41 ± 0.06, Cl abstraction 0.65 ± 0.1), CDCl3 (D abstraction 0.035 ± 0.01, Cl abstraction 0.723 ± 0.005), allyl bromide (Br abstraction 0.53 ± 0.04, allylation 0.25 ± 0.01). Collision rates were calculated and reaction efficiencies are also reported. This study represents the first quantitative measurement of the gas phase reactivity of a bridgehead radical and suggests that distonic radical anions are good models for the study of their elusive uncharged analogues. The Royal Society of Chemistry.

Disubstituted adamantyl derivative or pharmaceutically acceptable salt thereof, and pharmaceutical composition and kit for inhibiting the growth of cancer containing the same as an active ingredient

The present invention relates to: a disubstituted adamantyl derivative or a pharmaceutically acceptable salt thereof, and an anticancer pharmaceutical composition and a kit containing same as an active ingredient. The disubstituted adamantyl derivative according to the present invention suppresses the growth of cancer cells by targeting mitochondria ETC complex I and damaging the metabolism of cancer cells, and thus can be useful as an anticancer pharmaceutical composition that is a powerful therapeutic agent for cancer dependent on oxidative phosphorylation for producing ATP.

METHODS OF INDUCING AN ANTI-CANCER IMMUNE RESPONSE

A method or preparing immunologically primed cancer cells using cancer cells collected from a patient includes treating the collected cancer cells, ex vivo, with a toxic concentration of a compound that modifies sphingolipid metabolism, wherein the toxic concentration is sufficient to induce immunogenic cell death in the cancer cells. In an embodiment, the compound is 3-(4-Chloro-phenyl)-adamantane-1-carboxylic acid(pyridin-4-ylmethyl)-amide compound or a pharmaceutically acceptable salt thereof. In an embodiment, the immunologically primed cancer cells overexpress calreticulin on their surface. In an embodiment, the cancer cells are solid tumor cells. In an embodiment, the cancer cells are circulating tumor cells. In an embodiment, the method further comprises harvesting at least a portion of the immunologically primed cancer cells; and suspending the cells in phosphate-buffered saline. In an embodiment, the method further comprises shipping at least a portion of the immunologically primed cancer cells to a point of the patient's care.

Synthesis method of 3-amino-1-adamantanol

The invention discloses a synthesis method of 3-amino-1-adamantanol. Adamantanecarboxylic acid is used as a substrate, and the preparation method comprises the following steps of: (1) slowly adding adamantanecarboxylic acid into liquid bromine, and synthesizing 3-bromine-1-adamantanecarboxylic acid under the action of an anhydrous aluminum trichloride catalyst, (2) reacting the synthesized 3-bromine-1-adamantanecarboxylic acid with triethylamine, diphenyl azide phosphate and tert-butyl alcohol in an organic solvent at the temperature of 80-110 DEG C for 12-16 hours to synthesize 3-bromine-1-tert-butoxycarbonylamidated adamantine, (3) carrying out reflux reaction on the 3-bromine-1-tert-butoxycarbonylamidated adamantine in an excessive amount of hydrobromic acid solution with the molar concentration of 10% for 24-48 hours, and (4) adding the synthesized bromate type 3-amino-1-adamantanol into an equimolar sodium hydroxide solution, heating to 30 DEG C while stirring, cooling to separateout a solid, carrying out suction filtration, and carrying out vacuum drying to obtain the 3-amino-1-adamantanol. The method is simple in steps, easy to operate, environment-friendly, low in cost andhigh in yield, and has the characteristic of suitability for industrial production.

Azido-Adamantyl Tin Sulfide Clusters for Bioconjugation

We present a new versatile route toward biomolecule-functionalized tin sulfide clusters. A novel bifunctional orthogonal spacer was developed and used for the formation of a trifold azido-adamantyl-terminated cluster, serving as a building block for click reactions. The azido cluster was quantitatively bioconjugated via a strain-promoted 1,3-dipolar cycloaddition, affording a peptide-decorated cluster.

Compound containing adamantane structure and serving as SGLT-2 inhibitor

The invention relates to a compound serving as an SGLT-2 inhibitor. The compound comprises C-heteroside and an adamantane structure, and has good selectivity to SGLT-2.

NOVEL DISUBSTITUTED ADAMANTYL DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PRODUCTION METHOD FOR SAME, AND PHARMACEUTICAL COMPOSITION FOR SUPPRESSING CANCER METASTASIS COMPRISING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel disubstituted adamantyl derivative or the pharmaceutically acceptable salts thereof, a method for preparing the same, and a pharmaceutical anticancer or antimetastasis composition comprising the same as an active ingredient. The disubstituted adamantyl derivative of the present invention suppressed accumulation of HIF-1α, inhibiting the expression of the metastasis related protein Twist dose-dependently. Thus, the disubstituted adamantyl derivative of the invention is effective in inhibiting the expressions of the metastasis related proteins, β-catenin and RohA, and the EMT related genes such as MMP2 and MMP9, without cytotoxicity. Therefore, the disubstituted adamantyl derivative or the pharmaceutically acceptable salts thereof of the invention can be efficiently used as a pharmaceutical anticancer or antimetastasis composition.

SPHINGOSINE KINASE INHIBITOR PRODRUGS

The invention relates to prodrugs of hydroxyl-substituted adamantane compounds, pharmaceutical compositions thereof, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease

A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives

Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect.

SPHINGOSINE KINASE INHIBITORS

The invention relates to substituted adamantane compounds, pharmaceutical compositions thereof, processes for their preparation, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease.