- Method for preparing pharmaceutical intermediate of tryptophan derivative
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The synthesis method comprises the following steps: L - tryptophan derivatives are taken as starting materials, and esterification is carried out in sequence. The amidation, Boc protection, hydrolysis, amidation or sequential esterification, amidation, Boc protection, hydrogenation, hydrolysis, amidation yields a target product, a tryptophan derivative pharmaceutical intermediate. The preparation method has the advantages of cheap and easily available raw materials, environment friendliness, less process three wastes, accords with the idea of green pharmacy, mild reaction conditions, simple process, simple and convenient operation, high yield and purity and easy amplification and production.
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Paragraph 0086; 0088; 0091-0098
(2021/09/21)
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- An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds
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Herein, we describe the development of a simple, high yielding and stereocontrolled strategy for the synthesis of a series of triazolopiperazines and other biologically relevant fused scaffolds from optically active amino acids. This route was applied to the synthesis of 22 scaffolds containing new, previously inaccessible vectors and used to access a novel analogue of ganaplacide.
- Bond, Andrew D.,Hanby, Abigail R.,King, Thomas A.,Moss, Thomas A.,Sore, Hannah F.,Spring, David R.,Stewart, Hannah L.
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supporting information
p. 6818 - 6821
(2020/07/04)
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- Synthesis of tryptophans by Lewis acid promoted ring-opening of aziridine-2-carboxylates: Optimization of protecting group and Lewis acid
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The preparation of tryptophan derivatives through the Lewis acid promoted substitution of aziridine carboxylates with indole was found to be accompanied by a ring-expansion reaction to generate an oxazolidinone byproduct. The ratio of tryptophan to oxazol
- Tirotta, Ilaria,Fifer, Nathan L.,Eakins, Julia,Hutton, Craig A.
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p. 618 - 620
(2013/02/23)
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- Aerobic palladium(II)-catalyzed 5-endo-trig cyclization: An entry into the diastereoselective C-2 alkenylation of indoles with tri- and tetrasubstituted double bonds
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The endo trick: An endo ring closure onto the trigonal β carbon atom of α,β-unsaturated acceptors that are tethered to the indole nitrogen atom followed by amide cleavage enables the diastereoselective C-2 alkenylation of indoles with fully substituted double bonds. The carboxy group functions as a synthetically useful temporary tether (see scheme). Copyright
- Kandukuri, Sandeep R.,Schiffner, Julia A.,Oestreich, Martin
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supporting information; experimental part
p. 1265 - 1269
(2012/03/08)
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- Orthogonal protecting groups in the synthesis of tryptophanyl- hexahydropyrroloindoles
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The synthesis of various polycyclic systems containing aC 3a-Ni bond between a hexahydropyrrolo[2,3-b]indole and an indole tryptophan is described here. A series of experiments were performed to determine the best combination of five orthogonal protecting groups and the best reaction conditions for formation of said bond, which is a common feature among many recently discovered marine natural products.
- Ruiz-Sanchis, Pau,Savina, Svetlana A.,Acosta, Gerardo A.,Albericio, Fernando,Alvarez, Mercedes
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supporting information; experimental part
p. 67 - 73
(2012/01/15)
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- A favorable, narrow, δh Hansen-parameter domain for gelation of low-molecular-weight amino acid derivatives
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In recent years, the design of new low-molecular-weight gelators (LMWGs) has attracted considerable attention because of the interesting supramolecular architectures as well as industrial applications. In this context, the role of the organic solvent in d
- Curcio, Pasquale,Allix, Florent,Pickaert, Guillaume,Jamart-Gregoire, Brigitte
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scheme or table
p. 13603 - 13612
(2012/01/05)
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- NOVEL TRICYCLIC CHIRAL COMPOUNDS AND THEIR USE IN ASYMMETRIC CATALYSIS
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The present invention relates to a compound of general Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and R31 are independently —COOR3, —R4COOR3, —R4CHO, —R4COR3, —R4CONR5R6, —R4COX, —R4OP(═O)(OH)2, —R4P(═O)(OH)2), —R4C(O)C(R3)CR5R6 and —R4CO2COR3. In addition, R31 may also be hydrogen. R3, R5 and R6 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. R4 an aliphatic bridge with a main chain having 1 to about 20 carbon atoms, an alicyclic bridge, an aromatic bridge, an arylaliphatic bridge or an arylalicyclic bridge, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and X is halogen. In Formula (XX) R30 is —C(OH)R1R2 or —COOR14, wherein R1, R2 and R14 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si.
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Page/Page column 18-19
(2011/11/12)
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- Hexahydropyrrolo [2,3-b]indoles: A new class of structurally rigid tricyclic skeleton for oxazaborolidine-catalyzed asymmetric borane reduction
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A new class of structurally rigid tricyclic chiral ligands based on the hexahydropyrrolo [2,3b]indole skeleton has been rationally designed and the catalytic abilities in asymmetric catalysis have been shown in the enantioselective borane reduction of prochiral ketones to afford the chiral alcohols in excellent yields and high enantioselectivities (up to 97% ee).
- Xiao, Jian,Wong, Zhen Zhou,Lu, Yun Peng,Loh, Teck Peng
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supporting information; experimental part
p. 1107 - 1112
(2010/07/03)
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- Unexpected domino ring closure: highly stereoselective construction of a tetracyclic indole alkaloid ring system
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An unexpected highly stereoselective domino ring closure gave the tetracyclic indole alkaloid IV-2 in good yield in one hydrogenation step. Crown Copyright
- Xiao, Jian,Loh, Teck-Peng
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scheme or table
p. 7184 - 7186
(2009/04/10)
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- Copper-catalyzed cyclization of lodo-tryptophans: A straightforward synthesis of pyrroloindoles
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(Chemical Equation Presented) Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, afford
- Coste, Alexis,Toumi, Mathieu,Wright, Karen,Razafimahaleo, Vanessa,Couty, Francois,Marrot, Jerome,Evano, Gwilherm
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supporting information; scheme or table
p. 3841 - 3844
(2009/07/01)
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- Synthesis of a β-tetrapeptide analog as a mother compound for the development of matrix metalloproteinase-2-imaging agents
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Matrix metalloproteinase-2 (MMP-2) is an attractive target for the diagnosis of cancer and atherosclerosis in nuclear imaging. A cyclic decapeptide, cCTTHWGFTLC (cCTT), has been used as the mother compound for the development of MMP-2-imaging agents with high potency and selectivity. Most of radiolabeled derivatives of cCTT currently developed for in vivo studies of MMP-2, however, suffer from low accumulation in the target tissues, such as tumors. For enhanced in vivo stability and tissue penetration, we designed a linear β-tetrapeptide analog, H-β3-Phe-β-Ala- β3-Trp-β3-His-OH (1), to mimic cCTT. The component β-amino acids were prepared by reduction of N-protected α-amino acid methyl esters to the alcohols, followed by conversion into the cyanides, and subsequent hydrolysis. Compound 1 was obtained from these β-amino acids by the conventional solution method. In MMP-2 inhibition assay, compound 1 displayed desirably significant inhibition, which was comparable to cCTT. These findings suggest that compound 1 may serve as a mother compound in the design and development of in vivo MMP-2-imaging agents.
- Mukai, Takahiro,Suganuma, Noriko,Soejima, Kenta,Sasaki, Junichi,Yamamoto, Fumihiko,Maeda, Minoru
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p. 260 - 265
(2008/09/21)
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- Facile preparation of polymer-supported methyl sulfonate and its recyclable use for methylation of carboxylic acids and amines
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A simple and efficient one-pot procedure for the preparation of polymer-supported methyl sulfonate from the reaction of polymer-supported sulfonic acid with trimethyl orthoacetate was achieved, and it could be successfully used for efficient methylation of carboxylic acids, phosphonic acids, sulfinic acids, amines, thiol, and phenol. Moreover, the polymer reagent could be recovered, regenerated, and reused easily for the same reactions. Georg Thieme Verlag Stuttgart.
- Yoshino, Tomonori,Togo, Hideo
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p. 517 - 519
(2007/10/03)
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- A general synthesis of N-reverse-prenyl indoles
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A general method for the construction of N-reverse-prenyl indoles was established using copper catalyzed N-propargylation, the Lindlar hydrogenation of the acetylenic bond, and dehydrogenation with chemical manganese dioxide as key steps. The antifungal i
- Yokokawa, Fumiaki,Sugiyama, Hideyuki,Aoyama, Toyohiko,Shioiri, Takayuki
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p. 1476 - 1480
(2007/10/03)
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- A rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxypyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones
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A study was performed on the rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo-[2,3-b]indole skeleton. A two-step selenocyclisation-oxidative deselenation sequence was used for the synthesis. It is reported that many biologically active natural products are based on this structure, such as the sporidesmins and certain members of the brevianamide and okaramine families.
- Ley, Steven V.,Cleator, Ed,Hewitt, Peter R.
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p. 3492 - 3494
(2007/10/03)
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- Scandium perchlorate as a superior Lewis acid for regioselective ring opening of aziridine carboxylate with indoles
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In the synthesis of optically active tryptophan derivatives, Lewis acid-promoted coupling between indole and optically active serine-derived aziridine carboxylate is attractive because of the flexibility and convergence. Scandium perchlorate has been found to be a superior Lewis acid to the previously reported scandium triflate with respect to the yields as well as the regioselectivity of aziridine ring opening. The scope and limitation of this Lewis acid are also described.
- Nishikawa, Toshio,Kajii, Shigeo,Wada, Kyoko,Ishikawa, Miyuki,Isobe, Minoru
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p. 1658 - 1662
(2007/10/03)
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- Synthetic studies of N-reverse prenylated indole. An efficient synthesis of antifungal indole alkaloids and N-reverse prenylated tryptophan
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The efficient method for the synthesis of N-1,1-dimethyl-2-propenyl (reverse prenyl) indole was developed by the N-propargylation of the indoline, partial hydrogenation of the terminal alkyne, and oxidation to the indole using chemical manganese dioxide (
- Sugiyama, Hideyuki,Yokokawa, Fumiaki,Aoyama, Toyohiko,Shioiri, Takayuki
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p. 7277 - 7280
(2007/10/03)
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- Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in the enantiospecific preparation of α-methyltryptophan: Application in the preparation of carbon-14 labeled PD 145942 and PD 154075
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[2R-(2α,3aβ,8aβ)]-2,3,3a,8a-Tetrahydro-pyrrolo[2.3-b]indole-1,2,8 -tricarboxylic acid-1,8-dibenzyl ester 2-methyl ester, its [2S-(2β,3aα,8aα)]-isomer, and the tribenzyl ester analogs were prepared. From these [2,3-b]indole-1,2,8-tricarboxylic acid esters we accomplished a simple, high yielding preparation of enantiopure α-methyltryptophan and methyl ester derivatives. Using this protocol, we inexpensively made (R)-α-[14C]methyltryptophan methyl ester, and in subsequent reactions converted it into [1-(2-hydroxy-cyclohexylcarbamoyl)-2-(1H-indol-3-yl)-1 -[14C]methylethyl]carbamic acid adamantan-2-yl ester (PD 145942) and [2-(1H-indole-3-yl)-1-[14C]methyl-1(1-phenyl-ethylcarbamoyl)-ethyl]carbamic acid benzofuran-2-yl methyl ester (PD 154075). Both of these compounds are drug candidates in preclinical study for the treatment of anxiety and emesis respectively.
- Ekhato, I. Victor,Huang, Yun
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p. 1019 - 1038
(2007/10/03)
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- The Asymmetric Synthesis of Non-peptide CCK-A Receptor Agonists
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The asymmetric synthesis, CCK receptor binding affinities and CCK-A agonist properties of a novel series of non-peptide CCK-A receptor selective ligands is reported.
- Burgaud, B. G. M.,Horwell, D. C.,Pritchard, M. C.,Bernad, N.,Martinez, J.
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p. 1081 - 1084
(2007/10/02)
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- A Regio- and stereocontrolled total synthesis of (-)-indolactam-V
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(-)-Indolactam-V (IL-V) (1)-was prepared in 10 steps from L-tryptophan methyl ester in 17.1% overall yield. The key steps involve regiospecific thallation of the acylindole intermediate (4), followed by azide displacement and reduction to introduce the 13-amino group. Control of the C-11 stereocenter was achieved by SN2 displacement of the chiral inflate (10), derived from D-valine. The thallium mediated closure of dipeptide (17) did not provide an alternative route to IL-V.
- Kogan, Timothy P.,Somers, Todd C.,Venuti, Michael C.
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p. 6623 - 6632
(2007/10/02)
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- CONSTRUCTION OF OPTICALLY PURE TRYPTOPHANS FROM SERINE DERIVED AZIRIDINE-2-CARBOXYLATES
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The possibility of preparing optically pure tryptophan derivatives from various substituted indoles and (2R)- or (2S)-2-aziridinecarboxylates has been examined.Zinc triflate was found to be the only Lewis acid capable of bringing about this reaction in mo
- Sato, Kazuo,Kozikowski, Alan P.
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p. 4073 - 4076
(2007/10/02)
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- Synthesis of Oxazolylindole Alkaloids from Tryptamine and Tryptophan by Oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone
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When N-acyl derivatives of tryptamine and L-tryptophan methyl ester were treated with DDQ (2 equiv) in tetrahydrofuran or other anhydrous solvents, four consecutive reactions, dehydrogenation, nucleophilic cyclization, another dehydrogenation, and isomeri
- Yoshioka, Tadao,Mohri, Kunihiko,Oikawa, Yuji,Yonemitsu, Osamu
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p. 2252 - 2281
(2007/10/02)
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