L-1,2,3,4-Tetrahydronorharman-3-carboxylic acid
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L-1,2,3,4-Tetrahydronorharman-3-carboxylic acid

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L-1,2,3,4-Tetrahydronorharman-3-carboxylic acid (CAS# 42438-90-4) is a useful research chemical.

Category
L-Amino Acids
Catalog number
BAT-002160
CAS number
42438-90-4
Molecular Formula
C12H12N2O2
Molecular Weight
216.23
L-1,2,3,4-Tetrahydronorharman-3-carboxylic acid
IUPAC Name
(3S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms
L-Tpi-OH; (S)-1,2,3,4-Tetrahydronorharmane-3-carboxylic acid
Appearance
White to off-white powder
Purity
≥ 98 %
Density
1.4±0.1 g/cm3
Melting Point
289 ℃ (dec.)(lit.)
Boiling Point
485.0±45.0 ℃ at 760 mmHg
Storage
Store at 2-8 ℃
InChI
InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)/t10-/m0/s1
InChI Key
FSNCEEGOMTYXKY-JTQLQIEISA-N
Canonical SMILES
C1C(NCC2=C1C3=CC=CC=C3N2)C(=O)O
1. Series of 2D and 3D coordination polymers based on 1,2,3,4-benzenetetracarboxylate and N-donor ligands: synthesis, topological structures, and photoluminescent properties
Lai-Ping Zhang, Jian-Fang Ma, Jin Yang, Yuan-Yuan Pang, Ji-Cheng Ma Inorg Chem. 2010 Feb 15;49(4):1535-50. doi: 10.1021/ic9019553.
Nine new coordination polymers, namely, [Mn(2)(L)(H(2)O)(4)].H(2)O (1), [Cd(L)(0.5)(H(2)O)] (2), [Zn(5)(L)(2)(mu(3)-O)(2)(H(2)O)(4)].2H(2)O (3), [Zn(4)(L)(2)(mu(3)-O)(2)][Zn(H(2)O)(5)].2H(2)O (4), [Zn(2)(L)(biim-4)(0.5)(H(2)O)(3)].H(2)O (5), [Cd(2)(L)(bpy)(H(2)O)].2H(2)O.0.5(CH(3)CH(2)OH) (6), [Cu(2)(H(2)L)(2)(bpy)(2)] (7), [Cu(2)(L)(bpy)(H(2)O)] (8), and [Cu(2)(L)(bpy)(1.5)(H(2)O)(2.5)] (9), where H(4)L = 1,2,3,4-benzenetetracarboxylic acid, biim-4 = 1,1'-(1,4-butanediyl)bis(imidazole), and bpy = 4,4'-bipyridine, have been synthesized under hydrothermal conditions. Compound 1 displays a rare trinodal (3,4,7)-connected (4(2).6)(4(5).6)(4(7).6(8).8(6)) topology. 2 possesses an alpha-Po net. 3 is a novel 3D framework based on pentanuclear Zn(II) clusters. By adjustment of the pH values of the reaction mixture of 3 with a Na(2)CO(3) solution, a structurally different compound, 4, was obtained, which exhibits a 3D porous framework with the [Zn(H(2)O)(6)](2+) cations located in the channels. 5 is an unusual example of a trinodal (3,5)-connected network with a Schlafli symbol of (4(2).6)(6(2).8)(4(2).6(2).8(5).10), whereas 6, containing tetranuclear Cd(II) clusters, shows a rare (4,6)-connected (4(4).6(2))(2)(4(4).6(10).8) topology. 7 exhibits a unique polythreading network, while 8 displays a scarce trinodal (3,4,5)-connected self-penetrating network. In comparison with 8, the chiral compound 9 possesses an unprecedented tetranodal (2,4)-connected (7)(7(5).11)(6(2).7(3).8)(2)(6.7(4).10)(2) topology. The effects of the carboxylate ligands, the pH values, the reaction temperatures, the central metals, and the neutral ligands were elucidated. The IR spectra, thermogravimetric analysis, and luminescent properties for the compounds were also investigated.
2. Validation of 8-[123I]iodo-L-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid as an imaging agent for prostate cancer in experimental models of human prostate cancer
Samuel Samnick, Ursula Nestle, Mathias Wagner, Thierry Fozing, Andrea Schaefer, Michael D Menger, Carl-Martin Kirsch Nucl Med Biol. 2007 Jan;34(1):99-107. doi: 10.1016/j.nucmedbio.2006.10.013.
Introduction: Very few tracers are currently available for the detection and staging of prostate cancer with positron emission tomography and single-photon emission computed tomography. This study evaluates the potential of 8-[123I]iodo-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid [ITIC(OH)] as an imaging agent for prostate cancer in experimental models of human prostate cancer. Methods: ITIC(OH) was prepared by the IODO-GEN method, with 82+/-7% radiochemical yield and >99% radiochemical purity after high-performance liquid chromatography. Thereafter, ITIC(OH) was examined in CD-1 nu/nu mice engrafted with human PC-3 and DU-145 prostate cancer in the flank or orthotopically in the prostate. Bioevaluation involved examination of the in vivo stability and uptake characteristics of ITIC(OH) into tumors and different organs by dynamic in vivo analysis and gamma counting of organs of interest after dissection. Results: ITIC(OH) showed good in vivo stability for biological investigations and was primary cleared through urine. In vivo, ITIC(OH) accumulated highly and specifically in tumors, reaching 13.6+/-2.1% to 16.2+/-2.5% injected dose per gram (ID/g) in heterotopic tumors compared with 14.8+/-2.6% and 17.6+/-3.4% ID/g in orthotopic tumor engrafts at 60 and 240 min postinjection, respectively. In contrast, radioactivity uptake in the blood, spleen, liver and gastrointestinal tract was moderate and decreased with time, resulting in marked tumor-to-background and excellent visualization of tumors. Conclusion: These results suggest that ITIC(OH) is a promising candidate as radiotracer for detecting prostate cancer and warrants further studies in patients to ascertain its potential as an imaging agent for clinical use.
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