Category: indole-building-block

Wellers, Georges published the artcileExchange between S³⁵ of ammonium sulfate and S³² of indoxylsulfate in aqueous solution, Formula: C8H6KNO4S, the publication is Compt. rend. (1960), 1140-2, database is CAplus.

A solution of indoxylsulfate, isolated from the urine of rabbits fed indole and methionine, was added to a solution of (NH₄)₂S³⁵O₄, and after 48 hrs. the mixture was chromatographed for 15 hrs. The radioactivity on the paper was determined before and after spraying with Ehrlich’s reagent. The radioactivity appeared only in the indoxylsulfate spot. The authors believed that the transfer of radioactivity takes place between the sulfate ions rather than between the S atoms. Although direct esterification of phenols by mineral sulfates would explain the appearance of radioactivity in the conjugated sulfates of the urine of animals administered Na₂S³⁵O₄, the fact that exchange between (NH₄)₂SO₄ and indoxylsulfate does occur would indicate that the former may not be the full explanation.

Compt. rend. 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 C6H10O7, 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

Kitazaki, Hirotaro published the artcileA colorimetric assay of protein kinase activity based on peptide-induced coagulation of gold nanorods, Synthetic Route of 330161-87-0, the publication is Colloids and Surfaces, B: Biointerfaces (2012), 7-11, database is CAplus and MEDLINE.

The authors succeeded in applying gold nanorods (NRs) for the detection of protein kinase (PK) activity based on a substrate-induced coagulation mechanism. Because NRs have cationic surface charges due to surface-adsorbed cetyltrimethylammonium bromide (CTAB), phosphorylated substrate peptides, which gain augmented anionic charges by phosphorylation, induce coagulation of the NRs, resulting in a red-to-blue color change of the corresponding NR dispersion. A large absorption coefficient of the NRs at the near-IR region enabled clear-cut detection of the peptide-induced coagulation. IC₅₀ values of several inhibitors of c-Src kinase determined by the present assay are consistent with reported values.

Colloids and Surfaces, B: Biointerfaces published new progress about 330161-87-0. 330161-87-0 belongs to indole-building-block, auxiliary class Protein Tyrosine Kinase/RTK,Src, name is SU6656, and the molecular formula is C19H21N3O3S, Synthetic Route of 330161-87-0.

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

Ishii, H. published the artcileFischer indolization and its related compounds. VII. Development of abnormal Fischer indolization of o-methoxyphenylhydrazone to provide a synthetic method for useful indole derivatives possessing an active methine group at C-6 and novel 3,6′-biindole derivatives, SDS of cas: 20538-12-9, the publication is Tetrahedron (1973), 29(14), 1991-2003, database is CAplus.

o-MeOC6H4NHN:CMeCO2Et (I) with p-MeC6H4SO3H in C6H6 in the presence of MeCOCH2COR (R = Me and OEt) gave Et 6-(1-acetyl-2-oxopropyl)indole-2-carboxylate (II, R = Me) and Et α-acetyl-2-(ethoxycarbonyl)indole-6-acetate (II, R = OEt), resp. Under similar conditions, I with Et 6-chloroindole-2-carboxylate gave di-Et 6-chloro-3,6′-biindole-2,2′-dicarboxylate (III, R = Cl, R1 = OH) and Et 5-(p-tolylsulfonyloxy)indole-2-carboxylate. Similarly, I with Et 7-methoxyindole-2-carboxylate gave di-Et 7-methoxy-4,6′-biindole-2,2′-dicarboxylate and III (R = H, R1 = OMe).

Tetrahedron published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, SDS of cas: 20538-12-9.

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

Ishii, Hisashi published the artcileAbnormal Fischer indolization and its related compounds. XII. Synthesis of 3,6′-biindole, Application In Synthesis of 20538-12-9, the publication is Chemical & Pharmaceutical Bulletin (1979), 27(2), 346-50, database is CAplus.

Fisher indole reaction of Et indole-2-carboxylate with (E)-2-MeOC₆H₄NHN:CMeCO₂Et (I) in refluxing C₆H₆ containing MeC₆H₄SO₃H gave 12.2% Et 7-methoxyindole-2-carboxylate and 28.4% biindole II (R = CO₂Et). Saponification of II (R = CO₂Et) gave II (R = CO₂H) which was decarboxylated by heating in quinoline containing Cu-chromite to give 3,6′-diindole (II; R = H). Treatment of indole with I in refluxing C₆H₆ containing MeC₆H₄SO₃H gave 11.3% Z–I, 25.6% diindolylpropionate III, and 17.3% indole trimer IV.

Chemical & Pharmaceutical Bulletin published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Application In Synthesis of 20538-12-9.

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

Ishii, Hisashi published the artcileFischer indolization and its related compounds. VIII. Formation of 4-aminoindole derivatives on the Fischer indolization of 2-methoxyphenylhydrazone derivatives, Recommanded Product: Ethyl 7-methoxy-1H-indole-2-carboxylate, the publication is Chemical & Pharmaceutical Bulletin (1974), 22(9), 1981-9, database is CAplus.

Fischer indolization of Et pyruvate 5-chloro-2-methoxyphenylhydrazone with ZnCl2 gave Et 4-amino-6-chloroindole-2-carboxylate (I,R = 4-NH2R1 = 6-Cl) together with I (R = 5-Cl, 5-OMe, R1 = 6-Cl; R = 4-Cl, R1 =7-OMe). Cyclization of Et Pyruvate 2-methoxyphenylhydraxone with p-toluenesulfonic acid in the presence of malonate gave Et 4-(ethoxycarbonylacetamido)indole-2-carboxylate and di-Et 4-(ethoxycarbonylacetamido)-3,6′-biindole-2,2-dicarboxylate with I (R = H, R1 = 5-OMe, 7-OMe,5-O3SC6H4Me-p) and aminoindole product in the abnormal Fisher indolization of a 2-methoxyphenylhydrazone derivative is discussed.

Chemical & Pharmaceutical Bulletin published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Recommanded Product: Ethyl 7-methoxy-1H-indole-2-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

Ishii, Hisashi published the artcileFischer indolization and its related compounds. XIII. Measurement of the nuclear magnetic resonance spectra of ethyl indole-2-carboxylate derivatives using the shift reagent and its application, Name: Ethyl 7-methoxy-1H-indole-2-carboxylate, the publication is Yakugaku Zasshi (1979), 99(4), 413-20, database is CAplus and MEDLINE.

Proton NMR spectra of several Et indole-2-carboxylate derivatives in the presence of a shift reagent, tris(dipivalomethanato)-europium [Eu(DPM)₃], were measured in CDCl₃ and good straight lines were obtained on plotting induced shift vs. concentration of Eu(DPM)₃ for each signal. Application of the McConnell-Robertson equation to interpret pseudocontact shifts of the indole derivatives gave good agreement between measured and predicted shifts. The relation between substituents of indoles and the position of the coordinated Eu atom is discussed.

Yakugaku Zasshi published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Name: Ethyl 7-methoxy-1H-indole-2-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

Ishii, Hisashi published the artcileSubstitution and migration of methoxyl group in the Fischer indolization of ethyl pyruvate 2-methoxyphenylhydrazone, Computed Properties of 20538-12-9, the publication is Tetrahedron Letters (1970), 1181-4, database is CAplus.

The indolization of 2-MeOC6H4NHN:CMeCO2Et (I) with 3M HCl-EtOH gave Et 6-chloroindole-2-carboxylate, Et 7-methoxyindole-2-carboxylate (II), and Et 6-ethoxyindole-2-carboxylate. The treatment of I with BF3 in AcOH or AcOEt gave IIk, Et indole-2-carboxylate (III), and Et 5-methoxyindole-2-carboxylate (IV). The treatment of I with H2SO4, in AcOH gave II, III, and IV. A mechanism involving substitution and migration of the MeO group is discussed.

Tetrahedron Letters published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Computed Properties of 20538-12-9.

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

Ishii, Hisashi published the artcileFischer indolization and its related compounds. VI. Effect of reagents and substituent of the o-substituted phenylhydrazone on abnormal Fischer indolization, COA of Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1973), 21(7), 1495-505, database is CAplus.

Treatment of Et pyruvate 2-methoxyphenylhydrazone (I) with Lewis acid gave 5-substituted and/or 5-methoxyindoles with Et 7-methoxy-indole-2-carboxylate as the main product in contrast with the abnormal Fischer indolization of I. Differences of the acid strength of the reagent and of the electron d. on a benzene ring due to introduction of some other addnl. substituents was the determinant for the abnormal transformation.

Chemical & Pharmaceutical Bulletin published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, COA of Formula: C12H13NO3.

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

Ishii, Hisashi published the artcileFischer indolization and its related compounds. V. Indolization of ethyl pyruvate 2-methoxyphenylhydrazone and its N-methyl derivative with protic acids. Unpredictable products and the mechanism, Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1973), 21(7), 1481-94, database is CAplus.

Fischer indolization of Et pyruvate 2-methoxyphenylhydrazone (I) and its N-Me derivative with protic acids gives mainly 6-substituted indole derivatives formed by substitution of the MeO group of I with nucleophiles in the reaction medium. The mechanism involved the cation II as the key intermediate in the formation of the unexpected indole products.

Chemical & Pharmaceutical Bulletin published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Formula: C12H13NO3.

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

Chin, Chen-Ni published the artcileThe third transmembrane helix of the cannabinoid receptor plays a role in the selectivity of aminoalkylindoles for CB2, peripheral cannabinoid receptor, Name: 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone, the publication is Journal of Pharmacology and Experimental Therapeutics (1999), 291(2), 837-844, database is CAplus and MEDLINE.

Two subtypes of the human cannabinoid receptor have been identified. The CB1 receptor is primarily distributed in the central nervous system, whereas the CB2 receptor is associated with peripheral tissue, including the spleen. These two subtypes are also distinguished by their ligand-binding profiles. The goal of this study was to identify critical residues in transmembrane region III (TM3) of the receptors that contribute to subtype specificity in ligand binding. For this purpose, a chimeric cannabinoid receptor [CB1/2(TM3)] was generated in which the TM3 of CB1 was replaced with the corresponding region of CB2. These receptors were stably expressed in Chinese hamster ovary cells for evaluation. The binding affinities of CB1/2(TM3) and the wild-type CB1 receptor to several prototype ligands were similar with one notable exception: the chimeric receptor exhibited a 4-fold enhancement in binding affinity to WIN 55212-2 (K_d = 4.8 nM) relative to that observed with CB1 (K_d = 21.7 nM). Two addnl. aminoalkylindoles, JWH 015 and JWH 018, also bound the chimeric receptor (K_i = 1.0 μM and 1.4 nM, resp.) with higher affinity compared with the wild-type CB1 (K_i = 5.2 μM and 9.8 nM, resp.). Furthermore, the increase in binding affinities of the aminoalkylindoles were reflected in the EC₅₀ values for the ligand-induced inhibition of intracellular cAMP levels mediated by the chimeric receptor. This pattern mirrors the selectivity of WIN 55212-2 binding to CB2 compared with CB1. Site-specific mutagenesis of the most notable amino acid changes in the chimeric receptor, Gly195 to Ser and Ala198 to Met, revealed that the enhancement in WIN 55212-2 binding is contributed to by the Ser but not by the Met residue. The data indicate that the amino acid differences in TM3 between CB1 and CB2 play a critical role in subtype selectivity for this class of compounds

Journal of Pharmacology and Experimental Therapeutics published new progress about 2854-32-2. 2854-32-2 belongs to indole-building-block, auxiliary class GPCR/G Protein,Cannabinoid Receptor, name is 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone, and the molecular formula is C23H23ClN2O4, Name: 2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone.

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