Category: 20538-12-9

Chen, Huayan published the artcileDiscovery of 3-Substituted 1H-Indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT₁ Selective Antagonists, Name: Ethyl 7-methoxy-1H-indole-2-carboxylate, the publication is ACS Medicinal Chemistry Letters (2016), 7(3), 335-339, database is CAplus and MEDLINE.

The indole I was identified as a novel and highly potent and selective CysLT₁ antagonist with IC₅₀ values of 0.0059±0.0011 and 15±4 μM for CysLT₁ and CysLT₂, resp.

ACS Medicinal Chemistry 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, 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

Murakami, Yasuoki published the artcileA novel method for the debenzylation of protected indole nitrogen, Related Products of indole-building-block, the publication is Synthesis (1984), 738-40, database is CAplus.

The AlCl₃-catalyzed deprotection of indoles I (R = H, OMe, Cl, COMe; R¹ = OEt, Me) gave the resp. II. I (R = 7-Cl, R¹ = OEt) was stirred with AlCl₃ in C₆H₆ 30 min to give 66% II (R = 7-Cl, R¹ = OEt).

Synthesis 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

Murakami, Yasuoki published the artcileFischer indolization of ethyl pyruvate 2-bis(2-methoxyphenyl)hydrazone and new insight into the mechanism of Fischer indolization. Fischer indolization and its related compounds. XXVII., Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1995), 43(8), 1287-93, database is CAplus.

In connection with studies on the direction of cyclization in the Fischer indolization of substituted diphenylhydrazones, the Fischer indolization of Et pyruvate 2-bis(2-methoxyphenyl)hydrazone was carried out. The result showed that cyclization in Fischer indolization of diphenylhydrazone does not always proceed to the electron-richer nucleus, but depends on the conformation of the enehydrazine. Thus, the Fischer indolization should proceed via a [3,3] sigmatropic route, with an electronic effect.

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

Murakami, Yasuoki published the artcileSynthetic studies of indoles and related compounds. Part 16. Synthesis of linear ethyl 9-methoxy-1H-benz[f]indole-2-carboxylate, Synthetic Route of 20538-12-9, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1988), 3005-12, database is CAplus.

The preparation of the title compound (I) is reported. I has different phys. properties from those of the indole previously reported (Goldsmith, E. A. and Lindwall, H. G., 1953) as I. I was prepared via a Friedel-Crafts acylation of Et pyrrole-2-carboxylate with phthalic anhydride and by the room temperature AlCl₃-MeOPh induced debenzylation of N-benzylindoes, e.g., II, that contain a methoxy substituent.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) 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, Synthetic Route 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

Pappalardo, Giovanni published the artcileIndoles. II. Ultraviolet spectra of ar-mononitro-2,3-dimethylindoles, Category: indole-building-block, the publication is Gazzetta Chimica Italiana (1958), 564-73, database is CAplus.

cf. C.A. 52, 6312f. Ultraviolet spectra of indole (I), skatole (II), and 2,3-dimethylindole (III), and of 4-, 5-, 6-, 7-nitro-2,3-dimethylindoles (IV, V, VI, VII) were measured in C₆H₁₂, alc., 0.05N HCl and 0.05N NaOH and were tabulated. PhNHN:CMeEt cyclized with polyphosphoric acid according to Kissmann, et al. (C.A. 48, 5850e), the product steam-distilled, and the distillate converted to the nitroso derivative, m. 63.5-4.5° (dilute alc.), and reconverted gave pure III, m. 105.5-6.5° (petr. ether). 3-O₂NC₆H₄NHN:CMeEt (12.0 g.) cyclized with concentrated HCl, the product [m. 99.0-9.5° (dilute alc.)] chromatographed in 200 ml. C₆H₆ on Al₂O₃ (Brockmann), eluted successively with C₆H₆ and 1:10 C₅H₅NC₆H₆, and the fractions rechromatographed from C₆H₆ and crystallized gave 2.5 g. IV, m. 176.5-7.5° (C₆H₆ and dilute alc.), and 3.5 g. VI, m. 141-2° (alc.). Cyclization of 4-O₂NC₆H₄NHN:CMeEt [85%, m. 128-9° (dilute alc.)] with concentrated HCl and chromatography in C₆H₆ on Al₂O₃ gave V, m. 193-4°. Similarly 2-O₂NC₆H₄NHNH₂ condensed with MeCOEt gave 63% 2-O₂NC₆H₄NHN:CMeEt, m. 75.5-6.5° (alc.), cyclized with concentrated HCl to VII, m. 162.5-3.5°. The spectrum of III in C₆H₁₂ was similar to that of I and II and the variations were in accord with those predicted on the basis of the effect of Me on the indole system. The notable modifications produced by the introduction of NO₂ groups into the aromatic ring varied according to the position and IV and VI showed certain similarities, though all, with the exception of V, showed bathochromic shifts. The shift was particularly pronounced with VII and the results in general confirmed the hypothesis of significant effects of the NO₂ group on the conjugation of the 2 nuclei, with participation of the hetero atom.

Gazzetta Chimica Italiana 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, Category: 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

Pappalardo, Giovanni published the artcileIndoles. III. Ultraviolet spectra of methoxyindoles and of methoxyindole-2-carboxylic acids and esters, HPLC of Formula: 20538-12-9, the publication is Gazzetta Chimica Italiana (1958), 574-90, database is CAplus.

The ultraviolet spectra of indole (I), 3-, 4-, 5-, 6-, 7-methoxyindoles (II-VI), indole-2-carboxylic acid (VII), 1-, 3-, 4-, 5-, 6-, 7-methoxyindole-2-carboxylic acids (VIII-XIII), VII Et ester (XIV), VIII Me ester (XV), Et 3-, 4-, 5-, 6-, and 7-methoxyindole-2-carboxylates (XVI-XX) were measured in alc. and C₆H₆, and λ_maximum in A. (log ε) were tabulated. II-VI were also measured in 0.05N HCl and 0.05N NaOH. N-Hydroxyindole-2-carboxylic acid (prepared by Na-Hg reduction of ο-O₂NC₆H₄CH₂COCO₂H) methylated with MeI and NaOMe and the product (40%) crystallized (Et₂O-petr. ether) gave VIII, m. 186-7° (dilute Me₂CO), identical with the acid obtained by saponification of XV. XVI saponified in aqueous alkali and the product extracted with Et₂O gave IX, m. 147° (50% MeOH), unstable to exposure to air. Na₂S₂O₅ (2.8 g.) added portionwise to 5 g. 4,2,6-H₂N(O₂N)₂C₆H₂Me (XXI) in 25 ml. HNO₃ (d. 1.52) at 0°, kept 30 min., the solution poured into 50 ml. alc. at 0° containing 0.3 g. CuO, the mixture heated on a steam bath, steam-distilled to remove the 2,6-(O₂N)₂C₆H₃Me (XXII) formed, and the distillate extracted with Et₂O yielded 46% XXII. XXI (4 g.) in 70 ml. concentrated HCl at 0° diazotized with saturated aqueous NaNO₂ (1.5 g.), kept 30 min., treated with 20 ml. 50% H₃PO₂ previously cooled to -5, stirred 1 hr. at 0°, kept 24 hrs. at 0° and the diluted solution steam-distilled yielded 43% XXII. XXII reduced to 2,6-O₂N(H₂N)C₆H₃Me converted to 2,6-O₂N(MeO)C₆H₃Me, transformed to 2,6-O₂N-(MeO)C₆H₃CH₂COCO₂H and reduced with Fe(OH)₂ yielded 65% X, m. 235.5-36° (decomposition). Saponification of XVIII gave a quant. yield of XI, m. 199.5-200°. Reduction of 2,4-O₂N(MeO)C₆H₃CH₂COCO₂H and purification of the product (70%) by repeated precipitation from Et₂O with petr. ether gave crystalline XII, m. 196-7° (alc.). Similarly by the method of Reissert (C.A. 17, 3186) 2,3-O₂N(MeO)C₆H₃CH₂COCO₂H was converted to 65% XIII, m. 181.5-82° (dilute alc.). Esterification of VIII by refluxing in absolute alc. containing 15% dry HCl gave the corresponding Et ester as an unstable oil, and accordingly VIII was similarly esterified in MeOH to 75% XV, m. 67-8° (ligroine). XIV with Me₂SO₄ and NaOH yielded 90% XVI, m. 92-3° (ligroine). X esterified with alc. HCl yielded 83% XVII, m. 171.5-2.5° (dilute alc.). Absolute alc. (100 ml.) containing 1.5 ml. concentrated H₂SO₄ refluxed 10 hrs. with 10 g. 4-MeOC₆H₄NHN:CMeCO₂H [m. 139.5° (C₆H₆)] and the product (20%) crystallized (dilute alc.) gave XVIII, m. 156-6.5°. Esterification of XII with alc. HCl gave 83% ester, crystallized (dilute alc.) to give XIX, m. 135-6°. Similar esterification of XIII yielded 80% XX, m. 113.5-14.5° (after recovery by steam distillation), also produced by cyclization of 2-MeOC₆H₄NHN:CMeCO₂Et (m. 88.5-89°) with AcOH-H₂SO₄. Cyclization with dry HCl gave an unidentified indolic compound, m. 168°. IX (5 g.) and 0.7 g. Cu chromite heated at 200-10° in 30 ml. anhydrous quinoline, the cooled mixture poured onto cracked ice and HCl, extracted with Et₂O, the washed and dried extract evaporated, and the residue distilled at 115-17°/5 mm. and recrystallized (petr. ether) gave II, m. 69.5°; 1,3,5-(O₂N)₃(C₆H₃) addition compound, m. 171-2° (Et₂O). X similarly decarboxylated, extracted with Et₂O, and the product (58%) fractionally crystallized (petr. ether) gave III, m. 69.5-70.5°; picrate, m. 159-60° (C₆H₆). Similarly decarboxylation of XI, XII, and XIII and extraction of the products with Et₂O yielded 70, 40, and 80%, resp. IV, b₂ 124-5°, m. 55.5-56° (petr. ether-EtOH) (picrate, m. 143-3.5°); V, 142-4°, m. 92.5° (petr. ether-EtOH)(picrate, m. 132°); and VI, b₆ 122° [picrate, m. 154-5° (decomposition)]. The introduction of the MeO group more or less distinctly altered the spectral behavior of the indole nucleus owing to the inductive effect of the substituent which, in some instances, was superimposed on the weak mesomeric effects of the indole and indolenine chromophores. The spectral characteristics of the methoxyindole-2-carboxylic acids and esters were related to those of the chromophore-NH(C:C)_nC of pyrrole-2-carboxylic acid with maximum spectral influence when the substituent MeO group was canonically located.

Gazzetta Chimica Italiana 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, HPLC of Formula: 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

Subba Rami Reddy, S. R. published the artcileSynthesis and biological evaluation of indoles, Application of Ethyl 7-methoxy-1H-indole-2-carboxylate, the publication is Pharma Chemica (2015), 7(10), 309-319, database is CAplus.

Objective of this research was to synthesize and characterize indole derivatives Indole nucleus has antimicrobial activities. Different kind of indole ring derivatives were synthesized such as 3-((E)-2-nitrovinyl)-1H-indole, 2-(1H-indol-3-yl)ethanamine, N-(2-(1H-indol-3-yl)ethyl)benzamide, Me 2-(3-(2-(benzamido)ethyl)-1H-indol-1-yl)acetate, 2-(3-(2-(benzamido)ethyl)-1H-indol-1-yl)acetic acid, N-(2-(1-((2,3-dihydro-1H-inden-5-yl-carbamoyl)methyl)-1H-indol-3-yl)ethyl)benzamide, e.g., I [R = 4-indanyl, 5-indanyl]. Antifungal activity of compounds I [R = 4-indanyl, 5-indanyl] were also studied.

Pharma Chemica 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 C7H6Cl2, Application of 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

Koning, Nicolas R. published the artcileTotal Synthesis of (-)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines, Computed Properties of 20538-12-9, the publication is Journal of the American Chemical Society (2021), 143(50), 21218-21222, database is CAplus and MEDLINE.

Asym. construction of dithiodiketopiperazines on otherwise achiral scaffolds remains a pivotal synthetic challenge encountered in many biol. significant natural products. Herein, authors report the first total syntheses of (-)-glionitrin A/B and revise the absolute configurations. Emerging from the study is a novel oxidative sulfenylation of triketopiperazines that enables asym. formation of dithiodiketopiperazines on sensitive substrates. The concise route paves the way for further studies on the potent antimicrobial and antitumor activities of glionitrin A and the intriguing ability of glionitrin B to inhibit invasive ability of cancer cells.

Journal of the American Chemical Society 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. XXIV. Fischer indolization of ethyl pyruvate 2-(2-methoxyphenyl)phenylhydrazone, COA of Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1991), 39(3), 572-8, database is CAplus.

In order to clarify the mechanism of Fischer indolization of 2-methoxyphenylhydrazones, Fischer indolization of Et pyruvate 2-(2-methoxyphenyl)phenylhydrazone I was carried out with hydrochloric acid in ethanol and zinc chloride in acetic acid. The reactions proceeded smoothly to give N-arylindoles II (R = Ph, R¹ = R² = H; R¹ = Cl, R² = H; R¹ = H, R² = OMe; R = 2-MeOC₆H₄, R¹ = R² = H) and some chlorinated diphenylamine derivatives III (R³ = Cl, R⁴ = R⁵ = H; R³ = R⁵ = H, R⁴ = Cl; R³ = R⁴ = H, R⁵ = Cl, R³-R⁵ = H) as byproducts. Consideration of the indole products revealed that the Fischer indolization proceeded mainly at the unsubstituted Ph nucleus rather than at the 2-methoxyphenyl nucleus. This result is inconsistent with the previous result that Fischer indolization of diarylhydrazones proceeded at the electron-richer nucleus. The structures of the diphenylamines III were determined by chem. means and the mechanism of their formation 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, 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. XXIV. Fischer indolization of ethyl pyruvate 2-(2-methoxyphenyl)phenylhydrazone, COA of Formula: C12H13NO3, the publication is Chemical & Pharmaceutical Bulletin (1991), 39(3), 572-8, database is CAplus.

In order to clarify the mechanism of Fischer indolization of 2-methoxyphenylhydrazones, Fischer indolization of Et pyruvate 2-(2-methoxyphenyl)phenylhydrazone I was carried out with hydrochloric acid in ethanol and zinc chloride in acetic acid. The reactions proceeded smoothly to give N-arylindoles II (R = Ph, R¹ = R² = H; R¹ = Cl, R² = H; R¹ = H, R² = OMe; R = 2-MeOC₆H₄, R¹ = R² = H) and some chlorinated diphenylamine derivatives III (R³ = Cl, R⁴ = R⁵ = H; R³ = R⁵ = H, R⁴ = Cl; R³ = R⁴ = H, R⁵ = Cl, R³-R⁵ = H) as byproducts. Consideration of the indole products revealed that the Fischer indolization proceeded mainly at the unsubstituted Ph nucleus rather than at the 2-methoxyphenyl nucleus. This result is inconsistent with the previous result that Fischer indolization of diarylhydrazones proceeded at the electron-richer nucleus. The structures of the diphenylamines III were determined by chem. means and the mechanism of their formation 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, 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