cas 14028-68-3, 1-Isoquinolineacetic acid, 1,2,3,4-tetrahydro-6,7-dimethoxy-, ethyl ester | Articles data ｜lookchem

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14028-68-3

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Synthesis and biological evaluation of 3-alkyl-dihydrotetrabenazine derivatives as vesicular monoamine transporter-2 (VMAT2) ligands
In the search of new probes for in vivo brain imaging of vesicular monoamine transporter type 2 (VMAT2), we have developed an efficient synthesis of a novel series of 3-alkyl-dihydrotetrabenazine (DTBZ) derivatives. The affinity of VMAT2 was evaluated by an in vitro inhibitory binding assay using [125I]-iodovinyl-TBZ or [18F](+)-FP-DTBZ as radioligands in rat striatal tissue homogenates. New DTBZ derivatives exhibited moderate to good binding affinity to VMAT2. Among these new ligands, compound 4b showed the best affinity for VMAT2 (Ki = 5.98 nM) and may be a useful lead compound for future structure-activity studies.
Zheng, Pinguan,Lieberman, Brian P.,Choi, Seok Rye,Pl?essl, Karl,Kung, Hank F.
p. 3435 - 3438
(2011/06/24)

Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoqainolizidine alkaloid by using a domino process
The first enantioselective syntheses of the Ipecacuanha alkaloid emetine (1) and the Alangium alkaloid tubulosine (2) is described employing a domino Knoevenagel/hetero-Diels-Alder reaction and an enantioselective catalytic transfer hydrogenation of imines as key steps. Thus, hydrogenation of the imine 15 with the catalyst (R,R)-16 gives the tetrahydroisoquinoline 14 with 95% ee which was transformed into the aldehyde (1S)-7. The three-component domino reaction of (1S)-7 with 6 and 8 led to 19, which in a second domino process was treated with K2CO3 in methanol followed by a hydrogenation to give the benzoquinolizidine 4 together with the diastereomers 22 and 23 in a overall yield of 66%. Further transformation of 4 with the amines 3 and 5 yielded enantiopure emetine (1) and tubulosine (2), respectively. In addition, starting from 19 the novel benzoquinolizidine alkaloid 34 was synthesised; this compound resembles the vallesiachotamine alkaloid dihydroantirhin 31, which has not been isolated so far but probably must also exist in nature.
Tietze, Lutz F.,Rackelmann, Nils,Mueller
p. 2722 - 2731
(2007/10/03)

The Reaction of 3,4-Dihydroisoquinolines With Malonic Acid and Its Derivatives
The reaction of various 3,4-dihydroisoquinolines with malonic acid gives the corresponding 1,2,3,4-tetrahydro-1-isoquinolineacetic acids in good yield, while the reaction with cyanoacetic acid and malonic acid half ethyl ester affords 1,2,3,4-tetrahydro-1
Pelletier, Jeffrey C.,Cava, Michael P.
p. 474 - 477
(2007/10/02)

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Chemical Properties

Melting Point: 78-79℃
Boiling Point: 391.202 °C at 760 mmHg
Flash Point:190.392 °C
Density: 1.098 g/cm³
Storage Temp.:under inert gas (nitrogen or Argon) at 2–8 °C
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.505
PKA: 8.28±0.40(Predicted)
PSA: 56.79000
LogP: 2.17260

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