Tag: M.W=250-300

Blackwell, J. Henry published the artcileVisible-Light-Mediated Carbonyl Alkylative Amination to All-Alkyl 伪-Tertiary Amino Acid Derivatives, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Journal of the American Chemical Society (2021), 143(3), 1598-1609, database is CAplus and MEDLINE.

The all-alkyl 伪-tertiary amino acid scaffold represents an important structural feature in many biol. and pharmaceutically relevant mols. Syntheses of this class of mol., however, often involve multiple steps and require activating auxiliary groups on the nitrogen atom or tailored building blocks. A straightforward, single-step, and modular methodol. for the synthesis of all-alkyl 伪-tertiary amino esters was reported. This new strategy uses visible light and a silane reductant to bring about a carbonyl alkylative amination reaction that combines a wide range of primary amines, 伪-ketoesters, and alkyl iodides to form functionally diverse all-alkyl 伪-tertiary amino esters. Bronsted acid-mediated in situ condensation of primary amine and 伪-ketoester delivers the corresponding ketiminium species, which undergoes rapid 1,2-addition of an alkyl radical (generated from an alkyl iodide by the action of visible light and silane reductant) to form an aminium radical cation. Upon a polarity-matched and irreversible hydrogen atom transfer from electron rich silane, the electrophilic aminium radical cation is converted to an all-alkyl 伪-tertiary amino ester product. The benign nature of this process allows for broad scope in all three components and generates structurally and functionally diverse suite of 伪-tertiary amino esters that will likely have widespread use in academic and industrial settings.

Journal of the American Chemical Society published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Karishin, A. P. published the artcileCondensation of 5-chloro-6-fluoroacenaphthenequinone with 3-hydroxythionaphthene, its derivatives, and indoxyl, HPLC of Formula: 2642-37-7, the publication is Zhurnal Obshchei Khimii (1964), 34(9), 306-8, database is CAplus.

Indigoid dyes of structure I were prepared, where X is S or NH, R¹ is H or Me, R² is H, or R¹ + R² is benzo, and R³ is H, Cl, or OEt. 5-Chloro-6- fluoroacenaphthene (10 g.) in 150 ml. HOAc was heated to 100掳, 50 g. Na₂Cr₂O₇ was added, heating continued 4 min., and the mixture poured into 300 ml. H₂O. The precipitate was filtered, washed, and heated twice with 300 ml. 6% NaHC0₃ solution on a boiling water bath for 40 min. 4,5,1,8-ClFC₁₀H₄(CO₂H)₂ (II), precipitated by acidifying the alk. solution with HCl, was filtered and dried to yield 3.1 g. colorless needles of II anhydride (III), m. 234-5掳 (HOAc). The filtrate from the isolation of III was treated twice with 50 ml. 25% NaHSO₃. The resulting compound was decomposed with HCl, and the mixture was boiled to remove SO₂, then cooled, filtered, and dried to give 3.41 g. 5-chloro-6-fluoronaphthenequinone (IV) golden yellow needles, m. 241-2. To 0.01 mole IV in 50 ml. boiling HOAc were added 0.01 mole 3-hydroxythionaphthene and 5 drops concentrated HCl, and the mixture was boiled 5 min., cooled, and filtered to give 88.2% I (R¹ = R² = R³ = H, X = S), m. 284-5掳(PhNO₂)₂, 位max. 492 and 535 m渭. Other I (X = S) were prepared similarly (R¹, R₂, R₃, % yield, m.p., and 位_max in 渭 (PhCl) given): H, H, Cl, 81.5, 375-6掳, 480 and 515; Me, H, Cl, 77.3, 334-5%, 482 and 517; H, H, OEt, 61.2, 271-2掳 460 and 496; R¹ + R² = benzo, H, 61.5, 337-8掳, 464 and 510. To 2.34 g. IV in 50 ml. boiling HOAc was added a filtered solution of 18.6 g. 7% indoxyl melt in 60 ml. 70% HOAc. The mixture was boiled 5 min., then cooled to give 2.6 g. (74.4%) I (R¹ = R² = R³ = H, X = NH), m. 324-5掳 (PhNO₂), 位_max 552 and 571 m渭.

Zhurnal Obshchei Khimii published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, HPLC of Formula: 2642-37-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Sen, S. P. published the artcilePaper chromatography of plant-growth regulators and allied compounds, Formula: C8H6KNO4S, the publication is Physiologia Plantarum (1954), 98-108, database is CAplus.

The chromatog. behavior of a number of indole derivatives in several solvent systems is described, along with their detection by fluorescence in UV light and their color reactions with FeCl₃-HClO₄, p-dimethylaminobenzaldehyde, KNO₂-HNO₃, cinnamaldehyde-HCl, dichloroquinone chlorimide, and other reagents. The following compounds were tested: indole, 2-methylindole, 3-methylindole, 3-indolecarboxylic acid, 3-indoleacetic acid, 3-indolepropionic acid, 3-indolebutyric acid, 3-indolecarboxaldehyde, 3-indoleacetaldehyde, 3-indoleacetonitrile, 3-indolebutyronitrile, Et 3-indoleacetate, tryptophan, tryptamine, gramine, isatin, N-acetylisatin, dihydroxyindole, indican, indican glucoside, indoxylacetate, N-acetylindoxyl, indigotin, indigodisulfonate, indigotetrasulfonate, and indirubin. R_f values, as detected by spraying with bromocresol green, were also determined for a number of aromatic acids. These included 1-naphthaleneacetic acid; 2-naphthoxyacetic acid; phenylacetic acid; phenoxyacetic acid, and its 慰-chloro, p-chloro, 2,4-dichloro, and 3,4,5-trichloro derivatives; and benzoic acid and its following derivatives: 慰-bromo, m-bromo, p-bromo, 慰-chloro, m-chloro, p-chloro, 2,4-dichloro, 3,4-dichloro, 2,3,5-triiodo, m-hydroxy; p-hydroxy, 2,4-dihydroxy, 慰-amino, p-amino, 2,5-dinitro, 3,5-dinitro, 2-amino-5-chloro, and 2-chloro-5-nitro.

Physiologia Plantarum published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C9H7NO3, Formula: C8H6KNO4S.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Danieli, Bruno published the artcileFormal enantioselective synthesis of tacamonine starting from asymmetrized 2-substituted propane-1,3-diols, COA of Formula: C15H20N2O2, the publication is Tetrahedron: Asymmetry (1999), 10(20), 4057-4064, database is CAplus.

2-Substituted propanediols monoacetates, derived from enzymic asymmetrization of the corresponding diols, have been obtained in high yields and enantiomeric excesses by using lipases and vinyl acetate as both solvent and acylating agent. These chiral building blocks have been transformed into the advanced intermediate I, useful for the enantioselective synthesis of tacamane alkaloids.

Tetrahedron: Asymmetry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, COA of Formula: C15H20N2O2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Grover, Huck K. published the artcileThe Synthesis of 5,5-Disubstituted Piperidinones via a Reductive Amination-Lactamization Sequence: The Formal Synthesis of (±)-Quebrachamine, COA of Formula: C15H20N2O2, the publication is Synlett (2015), 26(6), 815-819, database is CAplus.

A preliminary investigation into the prospect of a common synthetic intermediate for the synthesis of a variety of indole alkaloids has led to a synthesis of substituted piperidinones and the corresponding piperidines. These common natural product cores are accessed via a reductive amination-lactamization sequence of di-Me 3-ethyl-3-formylpimelate. The synthetic utility of this initial study has been displayed in the formal synthesis of (±)-quebrachamine.

Synlett published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, COA of Formula: C15H20N2O2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Walpole, C. published the artcile2-Nitrophenylcarbamoyl-(S)-prolyl-(S)-3-(2-naphthyl)alanyl-N-benzyl-N- methylamide (SDZ NKT 343), a Potent Human NK₁ Tachykinin Receptor Antagonist with Good Oral Analgesic Activity in Chronic Pain Models, Application In Synthesis of 167015-84-1, the publication is Journal of Medicinal Chemistry (1998), 41(17), 3159-3173, database is CAplus and MEDLINE.

A lead compound which had sub-micromolar affinity for the rabbit NK₁ receptor but negligible affinity for rat NK₁ receptors, 2-MeOC₆H₄CH₂NHCS-Pro-NHCHPh₂, was discovered by directed screening. 2-Substitution in the ring of the benzylthiourea substituent in the initial lead was found to be important, and halogens (Cl, Br) in this position were found to improve affinity for the human receptor. The activity of a series of 2-halo-substituted benzylthioureas was then optimized by modification of the proline diphenylmethyl amide, guided by a simple conceptual model based on structural overlay between these early antagonists and NK₁ selective peptides. In this way, aromatic amino acid amides were identified which had improved affinity with respect to the starting diphenylmethyl (DPM) amides. The first sub-nanomolar ligand for the human NK₁ receptor which arose from this series, I, combined a 2-chlorobenzylthiourea unit with a 2-naphthylalanine amide. Contemporaneously it was discovered that the benzylthiourea unit could be simplified to a phenylthiourea providing that an appropriate 2-substituent was also incorporated. Combination of these two series gave 2-NO₂ phenylthiourea analogs which led directly to the analogous urea, II (SDZ NKT 343), a highly potent ligand for the human NK₁ receptor (K_i = 0.16 nM). In addition to its high in vitro potency, II proved to be a potent orally active analgesic in guinea pig models of chronic inflammatory and neuropathic pain. The nature of the 2-aryl substituent was found to be critical for oral activity in this series. Clin. evaluation of II as a novel analgesic agent is currently underway.

Journal of Medicinal Chemistry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C4H6BrFO2, Application In Synthesis of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Simpson, Levi S. published the artcileA cleavable scaffold strategy for the synthesis of one-bead one-compound cyclic peptoid libraries that can be sequenced by tandem mass spectrometry, SDS of cas: 167015-84-1, the publication is Tetrahedron Letters (2012), 53(18), 2341-2344, database is CAplus and MEDLINE.

Many macrocyclic depsipeptides or related compounds have interesting medicinal properties and often display more favorable pharmacokinetic properties than linear analogs. Therefore, there is considerable interest in the development of large combinatorial libraries of macrocyclic peptidomimetic compounds However, such mols. cannot be easily sequenced by tandem mass spectrometry, making it difficult to identify hits isolated from library screens using one bead one compound libraries. Here we report a strategy to solve this problem by placing a methionine in both the linker connecting the cyclic mol. to the bead as well as within the cycle itself. Treatment with CNBr both linearizes the mol. at a specific position and releases the mol. from the bead, making its characterization by tandem MALDI mass spectrometry straightforward.

Tetrahedron Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C23H23ClN2O4, SDS of cas: 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bergmann, Felix published the artcileDetermination of uric acid and its thio analogs in biological fluids, Computed Properties of 2642-37-7, the publication is Analytical Biochemistry (1965), 10(1), 73-85, database is CAplus and MEDLINE.

Uric acid and its thio derivatives were separated from plasma proteins by the use of Sephadex. Thiouric acids in plasma were determined spectrophotometrically. Uric acid analysis by enzymic oxidation was not disturbed by the presence of the 2- or 8-thio analog. On the other hand, separation of uric acid and its 6-thio derivative on an anion exchanger must precede determination of the former. The absorption spectra of the mercuric complexes of thiouric acids differed characteristically from the spectra of the free thio derivatives Analysis of thiouric acids in urine was based on the difference in absorbance between Hg(II)-free solutions and those containing the metal ion.

Analytical Biochemistry published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, Computed Properties of 2642-37-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Hayato, Yukitaka published the artcileIntroduction and recent achievements of the International Science and Engineering Fair (ISEF), Application of Potassium 1H-indol-3-yl sulfate, the publication is Kagaku to Kyoiku (2022), 70(1), 54-56, database is CAplus.

A review. In this paper, authors would like to introduce one of results of our activities, which was highly evaluated at ISEF2021, by Dr. Sotaka Hayato, Dr. Masafumi Kaneko, and Dr. Hitoshi Yoneaki of Naruto University of Education. The paper outlines award-winning research in ISEF2021 chem. division, its research and about announcement of ISEF2021. The final result was summarized as a research project “selective synthesis of indirubin and photocatalytic activity”, and received the Tokushima Prefectural Examination of Japan Student Science Award 2020.

Kagaku to Kyoiku published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, Application of Potassium 1H-indol-3-yl sulfate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Taddeini, L. published the artcileInhibition of the Ehrlich reaction of porphobilinogen by indican and related compounds, Safety of Potassium 1H-indol-3-yl sulfate, the publication is Clinica Chimica Acta (1962), 890-1, database is CAplus and MEDLINE.

From a study of the Ehrlich reaction of porphobilinogen (I) and related compounds, it was found that K indoxylsulfate (urinary indican) as well as certain other members of the indole series are markedly inhibitory. Because of the importance of this finding for detection of I in the urine, a study on the inhibitory effect of indican was made. The results revealed an inhibitory effect of indican on the I aldehyde color intensity, increasing from about 35% at a concentration of indican of 0.625 × 10^-4 millimole/ml. to over 85% at a concentration of 2.50 × 10^-4. Complete inhibition of the I aldehyde color reaction was obtained with an indican concentration of 5.00 × 10^-4. Indole and 5-hydroxyindoleacetic acid (II) are also inhibitory to about the same degree as indican. The inhibition was not due to complexing of indoles with I since the addition of the indole to the fully developed solution of the I-aldehyde compound also produced rapid fading of the color. The mechanism responsible for the inhibition is the nucleophilic addition of indoles to the I-aldehyde compound This yields a colorless intermediary, p-dimethylaminophenylpyrrylindolylmethane. Indican inhibits the Ehrlich reaction of opsopyrroledicarboxylic acid (III) to a lesser extent (35% as compared with 86% in a 2:1 molar ratio), and II has essentially no inhibitory effect under the same conditions. III is structurally similar to I except in lacking the α-aminomethyl group of the latter compound The much smaller inhibition of III thus suggests that the α-aminomethyl group (which is protonated in the presence of the Ehrlich reagent), activated the I-aldehyde compound with respect to nucleophilic attack of the indole. However, indole itself inhibits the aldehyde reaction of III to at least 95%, in a 2:1 molar ratio. Thus, it is evident that the character of the substituents of the indole is also a factor of importance. The present observations on the inhibition of the I-Ehrlich reaction by indican and other indolic compounds clarify the recent finding that an unknown inhibitor is present in some I-containing urines responsible for false neg. Ehrlich reactions.

Clinica Chimica Acta published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C7H5ClN2S, Safety of Potassium 1H-indol-3-yl sulfate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles