(S)-2-Tryptoline-3-carboxylic acid methyl ester
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(S)-2-Tryptoline-3-carboxylic acid methyl ester

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Category
Cyclic Amino Acids
Catalog number
BAT-006636
CAS number
79815-18-2
Molecular Formula
C13H14N2O2
Molecular Weight
230.28
(S)-2-Tryptoline-3-carboxylic acid methyl ester
IUPAC Name
methyl (3S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
Synonyms
H-Tpi-OMe; H-Thnh(3)-OMe; (S)-1,2,3,4-Tetrahydronorharman-3-carboxylic acid methyl ester; Methyl 1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate hydrochloride
Density
1.262±0.06 g/cm3(Predicted)
Melting Point
143-145 °C
Boiling Point
401.9±45.0 °C(Predicted)
Storage
Store at -20 °C
InChI
InChI=1S/C13H14N2O2/c1-17-13(16)11-6-9-8-4-2-3-5-10(8)15-12(9)7-14-11/h2-5,11,14-15H,6-7H2,1H3/t11-/m0/s1
InChI Key
QZGCHMZBGHVZFB-NSHDSACASA-N
Canonical SMILES
COC(=O)C1CC2=C(CN1)NC3=CC=CC=C23
1. Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid
Józef Kula, Radoslaw Bonikowski, Malgorzata Szewczyk, Kornelia Ciolak Chem Phys Lipids. 2014 Oct;183:137-41. doi: 10.1016/j.chemphyslip.2014.06.005. Epub 2014 Jun 20.
(R)-ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products.
2. Regioselective synthesis of 2,8-disubstituted 4-aminopyrido[3,2-d]pyrimidine-6-carboxylic acid methyl ester compounds
Gwenaelle Bouscary-Desforges, Agnes Bombrun, John Kallikat Augustine, Gérald Bernardinelli, Anna Quattropani J Org Chem. 2012 Jan 6;77(1):243-52. doi: 10.1021/jo201834d. Epub 2011 Dec 19.
We report herein the synthesis of 4-amino-2,8-dichloropyrido[3,2-d]pyrimidine derivatives 2 and their regioselective diversification through S(N)Ar and metal-catalyzed cross-coupling reactions. While amination of 2 took place selectively at C-2, the regioselectivity of thiol or thiolate addition depended on the reaction conditions. Selective C-8 addition was obtained in DMF with Hünig's base and C-2 addition in (i)PrOH. These C-2 or C-8 regioselective thiolations provided an opportunistic way to selectively activate either of the two positions toward the metal-catalyzed cross-coupling reaction. The chloride could be efficiently substituted by Suzuki-Miyaura reaction and the sulfanyl group by Liebeskind-Srogl cross-coupling reaction, demonstrating the orthogonality of both reactive centers. The development of regioselective conditions for these different transformations yielded the synthesis of 4-amino-2,6,8-trisubstituted pyrido[3,2-d]pyrimidine derivatives, with various substituents.
3. Evaluation of plant elicitation with methyl-jasmonate, salicylic acid and benzo (1,2,3)-thiadiazole-7-carbothioic acid-S-methyl ester for the sustainable management of the pine wilt disease
Adrián López-Villamor, Marta Nunes da Silva, Marta W Vasconcelos Tree Physiol. 2022 Dec 12;42(12):2596-2613. doi: 10.1093/treephys/tpac088.
Treatment with plant elicitors can be a promising method to induce Pinus pinaster tolerance against the pinewood nematode (PWN), Bursaphelenchus xylophilus, by promoting plant antioxidant system, micronutrient accumulation and by modulating plant-associated bacterial populations. To test this hypothesis, plants were sprayed with methyl jasmonate (MeJA), salicylic acid (SA) or benzo (1,2,3)-thiadiazole-7-carbothioic acid-S-methyl ester (BTH), and evaluated until 35 days after-inoculation (dai) for: i) extent of foliar symptoms; ii) nematode density inside stem tissues; iii) proxies for oxidative damage and antioxidant activity, iv) micronutrient concentration and v) bacterial diversity. Compared with non-elicited plants, plant elicitation, particularly with BTH, significantly decreased nematodes density inside stem tissues (by 0.63-fold). Concordantly, without elicitation plant mortality reached 12.5% while no mortality was observed in elicited plants. BTH-elicited plants had significantly higher concentrations of anthocyanins and carotenoids at the end of the assay than SA-elicited and MeJA-elicited plants, which possibly contributed to the lower PWN colonization and degree of foliar symptoms observed. Accordingly, MeJA and SA led to increased lipid peroxidation at 28 dai (by 2.64- and 2.52-fold, respectively) in comparison with BTH (by 1.10-fold), corroborating its higher potential in increasing plant antioxidative response during infection. Moreover, carotenoids showed a negative correlation with nematode migration, whereas polyphenols showed a positive correlation. Elicitors also induced changes in the bacterial community of infected P. pinaster plants, increasing the diversity of specific populations. Finally, elicitors induced significant changes in micronutrients accumulation in plant tissues, namely a decrease in the concentration of B, Mn and Ni in plants treated with BTH compared to those treated with the other elicitors. Altogether, results suggest that elicitation with MeJA, SA and, particularly, BTH, increases tolerance against B. xylophilus by promoting plant antioxidant system, changing the accumulation of essential micronutrients and modulating plant-associated bacterial diversity.
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