Category: 114527-53-6

Product Details of 114527-53-6. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid, is researched, Molecular C10H11NO2, CAS is 114527-53-6, about Catalytic Hydrogenation of Substituted Quinolines on Co-Graphene Composites. Author is Asaula, Vitalii M.; Buryanov, Volodymyr V.; Solod, Bohdan Y.; Tryus, Daryna M.; Pariiska, Olena O.; Kotenko, Igor E.; Volovenko, Yulian M.; Volochnyuk, Dmitriy M.; Ryabukhin, Sergey V.; Kolotilov, Sergey V..

A set of 20 composites was prepared by pyrolysis of Co2+ complexes with 1,10-phenanthroline, melamine and 1,2-diaminobenzene. These composites were tested as the catalysts for the hydrogenation of quinolines. As shown by powder X-ray diffraction and TEM, the composites contained Co particles of several dozen nm sizes. The composition (elements content), Raman spectra X-ray photoelectron spectra parameters of the composites were analyzed. It was found that there was no distinct factor that controlled the yield of 1,2,3,4-tetrahydroquinolines in the investigated process. The yields of the resp. products were in the range 90-100%. The three most active composites were selected for scale-up and hydrogenation of a series of substituted quinolines. Up to 97% yield of 1,2,3,4-tetrahydroquinoline was obtained on a 50 g scale. Five representative substituted quinolines were synthesized on a 10-20 g scale using the Co-containing composites as the catalysts.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Asaula, Vitalii M.; Buryanov, Volodymyr V.; Solod, Bohdan Y.; Tryus, Daryna M.; Pariiska, Olena O.; Kotenko, Igor E.; Volovenko, Yulian M.; Volochnyuk, Dmitriy M.; Ryabukhin, Sergey V.; Kolotilov, Sergey V. researched the compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid( cas:114527-53-6 ).Product Details of 114527-53-6.They published the article 《Catalytic Hydrogenation of Substituted Quinolines on Co-Graphene Composites》 about this compound( cas:114527-53-6 ) in European Journal of Organic Chemistry. Keywords: quinoline preparation catalytic hydrogenation cobalt graphene composite. We’ll tell you more about this compound (cas:114527-53-6).

A set of 20 composites was prepared by pyrolysis of Co2+ complexes with 1,10-phenanthroline, melamine and 1,2-diaminobenzene. These composites were tested as the catalysts for the hydrogenation of quinolines. As shown by powder X-ray diffraction and TEM, the composites contained Co particles of several dozen nm sizes. The composition (elements content), Raman spectra X-ray photoelectron spectra parameters of the composites were analyzed. It was found that there was no distinct factor that controlled the yield of 1,2,3,4-tetrahydroquinolines in the investigated process. The yields of the resp. products were in the range 90-100%. The three most active composites were selected for scale-up and hydrogenation of a series of substituted quinolines. Up to 97% yield of 1,2,3,4-tetrahydroquinoline was obtained on a 50 g scale. Five representative substituted quinolines were synthesized on a 10-20 g scale using the Co-containing composites as the catalysts.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetic sympatholytic substances in the ergotamine series. V. Some derivatives of 1,2,3,4-tetrahydroquinoline》. Authors are Chiavarelli, Stefano; Marini-Bettol, G. B..The article about the compound:1,2,3,4-Tetrahydroquinoline-3-carboxylic acidcas:114527-53-6,SMILESS:OC(=O)C1CNC2=CC=CC=C2C1).Category: thiazolidine. Through the article, more information about this compound (cas:114527-53-6) is conveyed.

cf. C.A. 46, 5602g. In connection with investigations aimed at establishing the relations between the chem. structure and biol. activity of compounds of the type of the alkaloids of Segale cornuta, it seemed of interest to study some 3-substituted derivatives of 1,2,3,4-tetrahydroquinoline (I), particularly since the structure of I is found in the lysergic acid mol. By a modification of the method of Gilman and Spatz (C.A. 35, 5495.2), 83 g. 3-quinolinecarboxylic acid (II), m. 275-6°, was obtained by refluxing 108 g. 3-cyanoquinoline (III) and 20% aqueous NaOH 2 hrs. The Na salt of II (25 g.) in 200 cc. water and 5 g. Raney Ni, hydrogenated 2 hrs. at 150° and 120 atm., filtered, the filtrate concentrated, acidified with HCl (d. 1.17) (to Congo red), and the precipitate purified by dilute EtOH yield 14 g. 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (IV), m. 236°, which with NH4OH yields the free acid, m. 145-6° (from EtOH). IV (0.2 g.) in 3 cc. anhydrous C5H5N and 1.6 g. Ac2O, refluxed 10 min., poured when cool into 10 cc. water + 6 cc. HCl, allowed to stand, and the precipitate purified by EtOH, yield the 1-Ac derivative, C12H14O2N, straw-colored, m. 152°. A suspension of 100 g. III in 1400 cc. MeOH refluxed 10 hrs. in a current of HCl gas (III.HCl forms first), most of the MeOH distilled, the residue poured into 3 l. ice-water, made alk. with K2CO3, kept ice-cold several hrs., and the precipitate purified by MeOH, yields 82 g. of Me 3-quinolinecarboxylate (V), m. 73-4°. V (36 g.) in 300 cc. MeOH with 5 g. Pd-C, hydrogenated at 60-65° under 90 atm., filtered, concentrated in vacuo, and allowed to stand, yields Me dihydro-3-quinolinecarboxylate (VI), m. 134-5°, is strongly fluorescent in Wood light (both solid and in solution), reduces neutral AgNO3 solution, is oxidized by dilute KMnO4; picrate, m. 187-9°. V (2 g.) in 50 cc. MeOH with 2 g. Raney Ni, hydrogenated 3 hrs. at 110° under 100 atm., filtered, and distilled at 115° (0.1 mm.); or 5 g. VI in 100 cc. MeOH with 4 g. Raney Ni and 1 g. 10% Pd-C, hydrogenated at 100° under 100 atm., and the product filtered, concentrated, and distilled in vacuo, yields the 1,2,3,4-tetrahydro derivative (VII), of VI, viscous oil, b0.3 124°. With HCl, it forms an HCl salt, m. 181-4°, and with picric acid a picrate, m. 151-3°. VII (1 g.) and 5-8 cc. concentrated HCl, heated in a sealed tube 3 hrs. at 100°, and the product purified by dilute EtOH, yield 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (VIII), m. 234°. N,N-Diethyl-3-quinolinecarboxamide (IX) (10 g.) in 100 cc. MeOH with 3 g. 10% Pd-C, hydrogenated 3 hrs. at 60° under 90 atm., filtered, concentrated, and the precipitate purified by EtOH, yields 1,2,3,4-tetrahydro derivative (X), m. 132-3°, forming with HCl a HCl salt, m. 160-1°. Hydrolyzed like VII, X yields VIII, m. 235-6°. 3-Aminoquinoline (XI) (144 g.) in 400 cc. tetrahydronaphthalene with 15 g. Raney Ni, hydrogenated at 55° under 90 atm., filtered, distilled in vacuo, and the residue rectified in vacuo, yields 127 g. crude product, b8 160-6°, which, fractionated and the fractions b. above 164° distilled in vacuo (0.8 mm.) at 250°, yields the 1,2,3,4-tetrahydro derivative (XII), m. 57°; picrate (from anhydrous EtOH), m. 205-6°; HCl salt (from EtOH by addition of Et2O), sinters 240°, m. 250°, turns violet by oxidation in air. XII oxidizes easily on exposure to air and light, and shows triboluminescence when rubbed with a wooden spatula. Benzoylated by the Schotten-Bauman method, XII gives a di-Bz derivative, C23H20O2N2, m. 201° (from EtOH). The distillation residue of XII (a fraction, b0.8 250°), fractionated further, gives a fraction, b0.4 234°, 3,3′-iminobis(1,2,3,4-tetrahydroquinoline) (XIII), very viscous resinous oil. With HCl, it forms a HCl salt (XIV), m. 254°, and with picric acid a picrate, m. 190-2°. In aqueous HCl solution, XIV gives with aqueous NaNO2 a yellow precipitate, which, purified by EtOH, yields the nitroso derivative, C18H18O3N6, m. 156°. Et2SO4 (9 cc.), added during 1 hr. to 15 g. XII in 200 cc. anhydrous Me2CO and 16 g. K2CO3, the mixture refluxed 6 hrs., filtered, evaporated, excess 20% aqueous NaOH added, the solution extracted with Et2O, the extract dried by K2CO3, evaporated, and the residue distilled in vacuo, yields 3-ethylamino-1,2,3,4-tetrahydroquinoline, b0.1 110-13°; picrate (from anhydrous EtOH), m. 198°. Et2SO4 (28 cc.), added during 1 hr. to 15 g. XII in 300 cc. anhydrous Me2CO and 48 g. K2CO3, the mixture refluxed 8 hrs., and the foregoing procedure followed, yields 3-diethylamino-1-ethyl-1,2,3,4-tetrahydroquinoline, b0.4 116°; picrate, m. 103-4°; HCl salt, very hygroscopic. The ultraviolet absorption spectra of II, IV, V, VI, VII, IX, X, XI, and XII are reproduced.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids, published in 2019-07-03, which mentions a compound: 114527-53-6, mainly applied to cyclic beta amino acid preparation electrophilic amination, Name: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid.

Electrophilic aminations involve an umpolung of a nitrogen atom, providing an alternate, distinctive synthetic strategy. The recent advent of various designed O-substituted hydroxylamines has significantly advanced this research field. An underappreciated issue is atom economy of the transformations: The necessary activating group on the oxygen atom is left in coproduced waste. Herein, the authors describe Rh-catalyzed electrophilic amination of substituted isoxazolidin-5-ones for the synthesis of unprotected, cyclic β-amino acids featuring either benzo-fused or spirocyclic scaffolds. Using the cyclic hydroxylamines allows for retaining both nitrogen and oxygen functionalities in the product. The traceless, redox neutral process proceeds on a gram scale with as little as 0.1 mol % catalyst loading. In contrast to related electrophilic aminations in the literature, a series of mechanistic experiments suggests a unique pathway involving spirocyclization, followed by the skeletal rearrangement. The insights provided herein shed light on a nuanced reactivity of the active species, Rh-nitrenoid generated from the activated hydroxylamine, and extend the knowledge on electrophilic aromatic substitutions.

Compound(114527-53-6)Name: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(1,2,3,4-Tetrahydroquinoline-3-carboxylic acid), if you are interested, you can check out my other related articles.

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Recommanded Product: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid, is researched, Molecular C10H11NO2, CAS is 114527-53-6, about Reduction of quinolinecarboxylic acids by Raney nickel. Author is Gracheva, I. N.; Tochilkin, A. I..

The heterocyclic nucleus of quinolinecarboxylic acids was reduced by Raney Ni in alkali media giving 1,2,3,4-tetrahydroquinoline-2-, -3-, -4-, -5-, -6-, and -8-carboxylic acids. Their Et esters were also prepared

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Reference:
Thiazolidine – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetic sympatholytic substances in the ergotamine series. V. Some derivatives of 1,2,3,4-tetrahydroquinoline》. Authors are Chiavarelli, Stefano; Marini-Bettol, G. B..The article about the compound:1,2,3,4-Tetrahydroquinoline-3-carboxylic acidcas:114527-53-6,SMILESS:OC(=O)C1CNC2=CC=CC=C2C1).Recommanded Product: 114527-53-6. Through the article, more information about this compound (cas:114527-53-6) is conveyed.

cf. C.A. 46, 5602g. In connection with investigations aimed at establishing the relations between the chem. structure and biol. activity of compounds of the type of the alkaloids of Segale cornuta, it seemed of interest to study some 3-substituted derivatives of 1,2,3,4-tetrahydroquinoline (I), particularly since the structure of I is found in the lysergic acid mol. By a modification of the method of Gilman and Spatz (C.A. 35, 5495.2), 83 g. 3-quinolinecarboxylic acid (II), m. 275-6°, was obtained by refluxing 108 g. 3-cyanoquinoline (III) and 20% aqueous NaOH 2 hrs. The Na salt of II (25 g.) in 200 cc. water and 5 g. Raney Ni, hydrogenated 2 hrs. at 150° and 120 atm., filtered, the filtrate concentrated, acidified with HCl (d. 1.17) (to Congo red), and the precipitate purified by dilute EtOH yield 14 g. 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (IV), m. 236°, which with NH4OH yields the free acid, m. 145-6° (from EtOH). IV (0.2 g.) in 3 cc. anhydrous C5H5N and 1.6 g. Ac2O, refluxed 10 min., poured when cool into 10 cc. water + 6 cc. HCl, allowed to stand, and the precipitate purified by EtOH, yield the 1-Ac derivative, C12H14O2N, straw-colored, m. 152°. A suspension of 100 g. III in 1400 cc. MeOH refluxed 10 hrs. in a current of HCl gas (III.HCl forms first), most of the MeOH distilled, the residue poured into 3 l. ice-water, made alk. with K2CO3, kept ice-cold several hrs., and the precipitate purified by MeOH, yields 82 g. of Me 3-quinolinecarboxylate (V), m. 73-4°. V (36 g.) in 300 cc. MeOH with 5 g. Pd-C, hydrogenated at 60-65° under 90 atm., filtered, concentrated in vacuo, and allowed to stand, yields Me dihydro-3-quinolinecarboxylate (VI), m. 134-5°, is strongly fluorescent in Wood light (both solid and in solution), reduces neutral AgNO3 solution, is oxidized by dilute KMnO4; picrate, m. 187-9°. V (2 g.) in 50 cc. MeOH with 2 g. Raney Ni, hydrogenated 3 hrs. at 110° under 100 atm., filtered, and distilled at 115° (0.1 mm.); or 5 g. VI in 100 cc. MeOH with 4 g. Raney Ni and 1 g. 10% Pd-C, hydrogenated at 100° under 100 atm., and the product filtered, concentrated, and distilled in vacuo, yields the 1,2,3,4-tetrahydro derivative (VII), of VI, viscous oil, b0.3 124°. With HCl, it forms an HCl salt, m. 181-4°, and with picric acid a picrate, m. 151-3°. VII (1 g.) and 5-8 cc. concentrated HCl, heated in a sealed tube 3 hrs. at 100°, and the product purified by dilute EtOH, yield 1,2,3,4-tetrahydro-3-quinolinecarboxylic acid-HCl (VIII), m. 234°. N,N-Diethyl-3-quinolinecarboxamide (IX) (10 g.) in 100 cc. MeOH with 3 g. 10% Pd-C, hydrogenated 3 hrs. at 60° under 90 atm., filtered, concentrated, and the precipitate purified by EtOH, yields 1,2,3,4-tetrahydro derivative (X), m. 132-3°, forming with HCl a HCl salt, m. 160-1°. Hydrolyzed like VII, X yields VIII, m. 235-6°. 3-Aminoquinoline (XI) (144 g.) in 400 cc. tetrahydronaphthalene with 15 g. Raney Ni, hydrogenated at 55° under 90 atm., filtered, distilled in vacuo, and the residue rectified in vacuo, yields 127 g. crude product, b8 160-6°, which, fractionated and the fractions b. above 164° distilled in vacuo (0.8 mm.) at 250°, yields the 1,2,3,4-tetrahydro derivative (XII), m. 57°; picrate (from anhydrous EtOH), m. 205-6°; HCl salt (from EtOH by addition of Et2O), sinters 240°, m. 250°, turns violet by oxidation in air. XII oxidizes easily on exposure to air and light, and shows triboluminescence when rubbed with a wooden spatula. Benzoylated by the Schotten-Bauman method, XII gives a di-Bz derivative, C23H20O2N2, m. 201° (from EtOH). The distillation residue of XII (a fraction, b0.8 250°), fractionated further, gives a fraction, b0.4 234°, 3,3′-iminobis(1,2,3,4-tetrahydroquinoline) (XIII), very viscous resinous oil. With HCl, it forms a HCl salt (XIV), m. 254°, and with picric acid a picrate, m. 190-2°. In aqueous HCl solution, XIV gives with aqueous NaNO2 a yellow precipitate, which, purified by EtOH, yields the nitroso derivative, C18H18O3N6, m. 156°. Et2SO4 (9 cc.), added during 1 hr. to 15 g. XII in 200 cc. anhydrous Me2CO and 16 g. K2CO3, the mixture refluxed 6 hrs., filtered, evaporated, excess 20% aqueous NaOH added, the solution extracted with Et2O, the extract dried by K2CO3, evaporated, and the residue distilled in vacuo, yields 3-ethylamino-1,2,3,4-tetrahydroquinoline, b0.1 110-13°; picrate (from anhydrous EtOH), m. 198°. Et2SO4 (28 cc.), added during 1 hr. to 15 g. XII in 300 cc. anhydrous Me2CO and 48 g. K2CO3, the mixture refluxed 8 hrs., and the foregoing procedure followed, yields 3-diethylamino-1-ethyl-1,2,3,4-tetrahydroquinoline, b0.4 116°; picrate, m. 103-4°; HCl salt, very hygroscopic. The ultraviolet absorption spectra of II, IV, V, VI, VII, IX, X, XI, and XII are reproduced.

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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

SDS of cas: 114527-53-6. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid, is researched, Molecular C10H11NO2, CAS is 114527-53-6, about Reduction of quinolinecarboxylic acids by Raney nickel. Author is Gracheva, I. N.; Tochilkin, A. I..

The heterocyclic nucleus of quinolinecarboxylic acids was reduced by Raney Ni in alkali media giving 1,2,3,4-tetrahydroquinoline-2-, -3-, -4-, -5-, -6-, and -8-carboxylic acids. Their Et esters were also prepared

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Reference of 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid, is researched, Molecular C10H11NO2, CAS is 114527-53-6, about Optimization of Small Molecules That Sensitize HIV-1 Infected Cells to Antibody-Dependent Cellular Cytotoxicity. Author is Grenier, Melissa C.; Ding, Shilei; Vezina, Dani; Chapleau, Jean-Philippe; Tolbert, William D.; Sherburn, Rebekah; Schon, Arne; Somisetti, Sambasivarao; Abrams, Cameron F.; Pazgier, Marzena; Finzi, Andres; Smith, Amos B..

With approx. 37 million people living with HIV worldwide and an estimated 2 million new infections reported each year, the need to derive novel strategies aimed at eradicating HIV-1 infection remains a critical worldwide challenge. One potential strategy would involve eliminating infected cells via antibody-dependent cellular cytotoxicity (ADCC). HIV-1 has evolved sophisticated mechanisms to conceal epitopes located in its envelope glycoprotein (Env) that are recognized by ADCC-mediating antibodies present in sera from HIV-1 infected individuals. Our aim is to circumvent this evasion via the development of small mols. that expose relevant anti-Env epitopes and sensitize HIV-1 infected cells to ADCC. Rapid elaboration of an initial screening hit using parallel synthesis and structure-based optimization has led to the development of potent small mols. that elicit this humoral response. Efforts to increase the ADCC activity of this class of small mols. with the aim of increasing their therapeutic potential was based on our recent cocrystal structures with gp120 core.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 114527-53-6, is researched, Molecular C10H11NO2, about Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids, the main research direction is cyclic beta amino acid preparation electrophilic amination.Application of 114527-53-6.

Electrophilic aminations involve an umpolung of a nitrogen atom, providing an alternate, distinctive synthetic strategy. The recent advent of various designed O-substituted hydroxylamines has significantly advanced this research field. An underappreciated issue is atom economy of the transformations: The necessary activating group on the oxygen atom is left in coproduced waste. Herein, the authors describe Rh-catalyzed electrophilic amination of substituted isoxazolidin-5-ones for the synthesis of unprotected, cyclic β-amino acids featuring either benzo-fused or spirocyclic scaffolds. Using the cyclic hydroxylamines allows for retaining both nitrogen and oxygen functionalities in the product. The traceless, redox neutral process proceeds on a gram scale with as little as 0.1 mol % catalyst loading. In contrast to related electrophilic aminations in the literature, a series of mechanistic experiments suggests a unique pathway involving spirocyclization, followed by the skeletal rearrangement. The insights provided herein shed light on a nuanced reactivity of the active species, Rh-nitrenoid generated from the activated hydroxylamine, and extend the knowledge on electrophilic aromatic substitutions.

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Quality Control of 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid, is researched, Molecular C10H11NO2, CAS is 114527-53-6, about Structure-based design of 3-carboxy-substituted 1,2,3,4-tetrahydroquinolines as inhibitors of myeloid cell leukemia-1 (Mcl-1). Author is Chen, L.; Wilder, P. T.; Drennen, B.; Tran, J.; Roth, B. M.; Chesko, K.; Shapiro, P.; Fletcher, S..

Mcl-1 has recently emerged as an attractive target to expand the armamentarium in the war on cancer. Using structure-based design, 3-carboxy-substituted 1,2,3,4-tetrahydroquinolines were developed as a new chemotype to inhibit the Mcl-1 oncoprotein. The most potent compound inhibited Mcl-1 with a Ki of 120 nM, as determined by a fluorescence polarization competition assay. Direct binding was confirmed by 2D 1H-15N HSQC NMR spectroscopy with 15N-Mcl-1, which indicated that interactions with R263 and T266, and occupation of the p2 pocket are likely responsible for the potent binding affinity. The short and facile synthetic chem. to access target mols. is expected to mediate lead optimization.

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