120686-08-0

Basic information

• Product Name: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-
• Synonyms: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-;7,8-dihydro-1H-spiro[[1,3]dioxolane-2,6-quinolin]-2(5H)-one
• CAS NO: 120686-08-0
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23
• Mol File: 120686-08-0.mol

Chemical Properties

• Melting Point: 250 °C (decomp)
• Boiling Point: 493.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• PKA: 12.91±0.20(Predicted)
• CAS DataBase Reference: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-(120686-08-0)
• EPA Substance Registry System: Spiro[1,3-dioxolane-2,6'(2'H)-quinolin]-2'-one, 1',5',7',8'-tetrahydro-(120686-08-0)

Safety Data

• Hazardous Substances Data: 120686-08-0(Hazardous Substances Data)

Upstream product

• 4746-97-8 cyclohexanedione monoethylene ketal 
• 3510-44-9 methyl cis-2-chloroacrylate 
• 922-67-8 propynoic acid methyl ester 
• 57440-57-0 1-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyrrolidine 
• 16490-68-9 2-chloroacrylamide 
• 128562-36-7 7-((dimethylamino)methyl)-1,4-dioxaspiro[4.5]decan-8-one 
• 41220-29-5 N-carbamoylmethylpyridinium chloride 
• 120685-98-5 1',5',7',8'-tetrahydro-1'-(phenylmethyl)spiro<1,3-dioxolane-2,6'(2'H)-quinolin>-2'-one 
• 105-37-3 Ethyl propionate 
• 144810-01-5 1,4-cyclohexanedione-1-ethylene acetal 4-trimethylsilyl enol ether 
• 285139-08-4 7-((dimethylamino)methylene)-1,4-dioxaspiro[4.5]decane-8-one 

Downstream Products

• 167557-63-3 2-Benzylamino-7,8-dihydro-5H-quinolin-6-one 
• 167557-61-1 7',8'-dihydro-N-(phenylmethyl)spiro<1,3-dioxolane-2,6'(5'H)-quinolin>-2'-amine 
• 167557-64-4 N²-Benzyl-N⁶-propyl-5,6,7,8-tetrahydro-quinoline-2,6-diamine 
• 167557-62-2 N²-benzyl-N⁶,N⁶-dipropyl-5,6,7,8-tetrahydroquinoline-2,6-diamine 
• 167557-65-5 N-(2-Benzylamino-5,6,7,8-tetrahydro-quinolin-6-yl)-N-propyl-propionamide 
• 120786-18-7 (+/-)-huperzine 
• 116-28-9 (-)-huperzine A 
• 123435-97-2 5,6,7,8-tetrahydro-2-methoxy-6-oxo-5-quinolinecarboxylic acid methyl ester 
• 120686-09-1 2-methoxy-6-oxo-5,6,7,8-tetrahydroquinoline 
• 167557-60-0 7',8'-dihydrospiro<1,3-dioxolane-2,6'(5'H)-quinolin>-2'-yl 4-methylbenzenesulfonate 

Relevant articles and documents

Synthesis of a hybrid analog of the acetylcholinesterase inhibitors huperzine A and huperzine B

The synthesis of a new hybrid analog of the acetylcholinesterase (AChE) inhibitors huperzine A and B is reported. An intramolecular reductive dicarbonyl coupling was used as a key reaction for constructing the tetracyclic ring system.

A tacrine-tetrahydroquinoline heterodimer potently inhibits acetylcholinesterase activity and enhances neurotransmission in mice

Cholinergic neurons are ubiquitous and involved in various higher brain functions including learning and memory. Patients with Alzheimer's disease exhibit significant dysfunction and loss of cholinergic neurons. Meanwhile, such cholinergic deficits can be potentially relieved pharmacologically by increasing acetylcholine. Acetylcholinesterase (AChE) inhibitors have been used to improve cholinergic transmission in the brain for two decades and have proven effective for alleviating symptoms in the early stages of Alzheimer's disease. Therefore, the search for AChE inhibitors for drug development is ongoing. The enzymatic pocket of AChE has long been the target of several drug designs over the last two decades. The peripheral and catalytic sites of AChE are simultaneously bound by several dimeric molecules, enabling more-efficient inhibition. Here, we used 6-chlorotacrine and the tetrahydroquinolone moiety of huperzine A to design and synthesize a series of heterodimers that inhibit AChE at nanomolar potency. Specifically, compound 7b inhibits AChE with an IC50 1 nM and spares butyrylcholinesterase. Administration of 7b to mouse brain slices restores synaptic activity impaired by pirenzepine, a muscarinic M1-selective antagonist. Moreover, oral administration of 7b to C57BL/6 mice enhances hippocampal long-term potentiation in a dose-dependent manner and is detectable in the brain tissue. All these data supported that 7b is a potential cognitive enhancer and is worth for further exploration.

A process for the preparation of the intermediates of the synthesis method of the huperzine-a

The invention discloses a synthesis method for preparing a huperzine A intermediate, which comprises the following steps: carrying out substitution at the alpha site of the carbonylic group by using 1,4-cyclohexyl diketone ethylene glycol and N,N-dimethylformamide dimethyl acetal as raw materials to obtain a substitution product, cyclizing the substitution product under the action of methyl cyanoacetate to obtain a cyclization product, and decarboxylating the cyclization product under the action of a strong base to obtain 2-carbonyl-6-ethylene ketal-5,7,8-dihydro-quinoline. The method has the advantages of fewer synthesis reaction steps, mild reaction conditions, low requirements for operating personnel and low environmental pollution, greatly lowers the raw material cost, and is simple to operate and convenient for refinement; and the obtained 2-carbonyl-6-ethylene ketal-5,7,8-dihydro-quinoline has high quality and high yield.

A 2-methoxy-6-one -5, 6, 7, 8-tetrahydro-quinoline synthesis method

The invention discloses a synthesis method of a drug intermediate 2-methoxy-6-one-5,6,7,8-tetrahydroquinoline. 1,4-cyclohexyldione monoethylene ketal used as the raw material is subjected to five-step reaction to generate the important intermediate 2-meth

Development of a large-scale synthetic route to manufacture (-)-huperzine A

A safe, practical and scalable process for manufacture of (-)-huperzine A has been developed and scaled up to manufacture several hundred grams of (-)-huperzine A with chemical and optical purity of >99%. The process consists of 11 chemical stages starting from commercially available materials with only nine isolation steps and no chromatography purification. This process provides a reliable and cost-effective source of synthetic (-)-huperzine A and its derivatives for pharmaceutical and nutraceutical markets.

METHOD OF PREPARING HUPERZINE A AND DERIVATIVES THEREOF

The present invention is related to the synthesis of huperzine A. The synthesis includes a variety of process steps that increase productivity, reduce safety concerns, and allow for increasing production of compounds of desired optical isomer. The inventive methods may encompass a single improved reaction step that may be incorporated into a known reaction process for synthesizing huperzine A or a derivative thereof to improve the overall reaction. The inventive methods also encompass complete synthesis methods for preparing huperzine A or a derivative thereof.

Heterodimers and Methods of Using Them

Novel heterodimers of tetrahydroacridines and tetrahydroquinolinones are disclosed. The heterodimers are capable of acting as both acetylcholinesterase inhibitors and N-methyl-D-aspartate (NMDA) receptor antagonists. The heterodimers may be used to improve cognitive defects via treatment or prevention in both humans and non-humans.

Racemic huperzine A

The present invention relates to racemic huperzine A, a pharmaceutical composition comprising huperzine A, its use as a medicament and for the manufacture of a medicament for the inhibition of the cholesterase enzymes in a mammal.

Synthesis and stereochemistry of 2-methyl-4H-9,12-dioxa-1,4-diazadispiro[5.2.5.2]tetradec-1-EN-3-one and its 2H-imidazolo-2-spirocyclohexane analogue. An anomalous michael type cyclocondensation

Starting from 1,4-cyclohexanedione monoethylene ketal and methyl propiolate in ammonia-saturated methanol at 100°C we obtained 2-methyl-4H-9,12-dioxa-1,4-diazadispiro[5.2.5.2]tetradec-1-en-3-one which was subsequently transformed into its O-methyl ether - a 2H-imidazolo-2-spirocyclohexane derivative. The mechanism of formation of this new heterocyclic system by anomalous Michael type cyclocondensation was proposed.

Synthesis and dopaminergic activity of pyridine analogs of 5-hydroxy-2- (di-n-propylamino)tetralin

The pyridine analogs of 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH- DPAT), 4-6, were synthesized, and their biological activity was compared to that of 5-OH-DPAT. Compounds 4 and 6 exhibited activity similar to 5-OH-DPAT in dopamine (DA) D2 a