Tag: M.W=200-250

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

Ren, Long published the artcileCarboxylic Acid-Promoted Single-Step Indole Construction from Simple Anilines and Ketones via Aerobic Cross-Dehydrogenative Coupling, Related Products of indole-building-block, the publication is Journal of Organic Chemistry (2018), 83(23), 14472-14488, database is CAplus and MEDLINE.

The cross-dehydrogenative coupling (CDC) reaction is an efficient strategy for indole synthesis. However, most CDC methods require special substrates, and the presence of inherent groups limits the versatility for further transformation. A carboxylic acid-promoted aerobic catalytic system is developed herein for a single-step synthesis of indoles from simple anilines and ketones. This versatile system is featured by the broad substrate scope and the use of ambient oxygen as an oxidant and is convenient and economical for both laboratory and industry applications. The existence of the labile hydrogen at C-3 and the highly transformable carbonyl at C-2 makes the indoles versatile building blocks for organic synthesis in different contexts. Computational studies based on the d. functional theory (DFT) suggest that the rate-determining step is carboxylic acid-assisted condensation of the substrates, rather than the functionalization of aryl C-H. Accordingly, a pathway via imine intermediates is deemed to be the preferred mechanism. In contrast to the general deduction, the in situ formed imine, instead of its enamine isomer, is believed to be involved in the first ligand exchange and later carbopalladation of the α-Me, which shed new light on this indolization mechanism.

Journal of Organic Chemistry 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, Related Products of indole-building-block.

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

Wen, Hui published the artcileDesign and synthesis of indoleamine 2,3- Dioxygenase 1 inhibitors and evaluation of their use as anti-tumor agents, Application of 6-Nitro-1H-indole-3-carboxylic acid, the publication is Molecules (2019), 24(11), 2124, database is CAplus and MEDLINE.

Indoleamine 2,3-dioxygenase (IDO) 1 is the key enzyme for regulating tryptophan metabolism and is an important target for interrupting tumor immune escape. In this study, we designed four series of compounds as potential IDO1 inhibitors by attaching various fragments or ligands to indole or phenylimidazole scaffolds to improve binding to IDO1. The compounds were synthesized and their inhibitory activities against IDO1 and tryptophan 2,3-dioxygenase were evaluated. Two compounds with a phenylimidazole scaffold (DX-03-12 and DX-03-13) showed potent IDO1 inhibition with IC₅₀ values of 0.3-0.5μM. These two IDO1 inhibitors showed low cell cytotoxicity, which indicated that they may exert their anti-tumor effect via immune modulation. Compound DX-03-12 was investigated further by determining the in vivo pharmacokinetic profile and anti-tumor efficacy. The pharmacokinetic study revealed that DX-03-12 had satisfactory properties in mice, with rapid absorption, moderate plasma clearance (~36% of hepatic blood flow), acceptable half-life (~4.6 h), and high oral bioavailability (~96%). Daily oral administration of 60 mg/kg of compound DX-03-12 decreased tumor growth by 72.2% after 19 days in a mouse melanoma cell B16-F10 xenograft model compared with the untreated control. Moreover, there was no obvious weight loss in DX-03-12-treated mice. In conclusion, compound DX-03-12 is a potent lead compound for developing IDO1 inhibitors and anti-tumor agents.

Molecules published new progress about 10242-03-2. 10242-03-2 belongs to indole-building-block, auxiliary class Indole,Nitro Compound,Carboxylic acid,Indole, name is 6-Nitro-1H-indole-3-carboxylic acid, and the molecular formula is C8H14O2, Application of 6-Nitro-1H-indole-3-carboxylic acid.

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

Martin, James S. published the artcileSynthesis of a Series of Diaminoindoles, HPLC of Formula: 10242-03-2, the publication is Journal of Organic Chemistry (2021), 86(17), 11333-11340, database is CAplus and MEDLINE.

A selection of 3,4-diaminoindoles were required for a recent drug discovery project. To this end, a 10-step synthesis was developed from 4-nitroindole. This synthesis was subsequently adapted and used to synthesize 3,5-; 3,6-; and 3,7-diaminoindoles from the corresponding 5-, 6-, or 7-nitroindole. These novel intermediates feature orthogonal protecting groups that allow them to be further diversified. This is the first reported synthesis of these types of compounds

Journal of Organic Chemistry published new progress about 10242-03-2. 10242-03-2 belongs to indole-building-block, auxiliary class Indole,Nitro Compound,Carboxylic acid,Indole, name is 6-Nitro-1H-indole-3-carboxylic acid, and the molecular formula is C9H6N2O4, HPLC of Formula: 10242-03-2.

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