Tag: M.W=200-250

Qiu, Di published the artcileDirect synthesis of arylboronic pinacol esters from arylamines, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Organic Chemistry Frontiers (2014), 1(4), 422-425, database is CAplus.

A metal-free synthetic method based on Sandmeyer-type transformation for preparation of arylboronic pinacol esters from easily available aromatic amines as starting materials was described. This novel transformation affords borylation products in good yields under mild reaction conditions. This strategy can be easily carried out in gram-scale, demonstrating the practical usefulness of the method. Moreover, the Sandmeyer-type transformation can be followed by Suzuki-Miyaura cross-coupling reaction without purification of the arylboronate products.

Organic Chemistry Frontiers published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

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

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

Lin, Shu-Yu published the artcilePhenyl Benzenesulfonylhydrazides Exhibit Selective Indoleamine 2,3-Dioxygenase Inhibition with Potent in Vivo Pharmacodynamic Activity and Antitumor Efficacy, Product Details of C9H8ClNO3S, the publication is Journal of Medicinal Chemistry (2016), 59(1), 419-430, database is CAplus and MEDLINE.

Tryptophan metabolism has been recognized as an important mechanism in immune tolerance. Indoleamine 2,3-dioxygenase plays a key role in local tryptophan metabolism via the kynurenine pathway and has emerged as a therapeutic target for cancer immunotherapy. The prior study identified Ph benzenesulfonyl hydrazide as a potent in vitro (though not in vivo) inhibitor of indoleamine 2,3-dioxygenase. Further lead optimization to improve in vitro potencies and pharmacokinetic profiles resulted in N’-(4-bromophenyl)-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl hydrazide (I), which demonstrated 59% oral bioavailability and 73% of tumor growth delay without apparent body weight loss in the murine CT26 syngeneic model, after oral administration of 400 mg/kg. Accordingly, I is proposed as a potential drug lead worthy of advanced preclin. evaluation.

Journal of Medicinal Chemistry published new progress about 166883-20-1. 166883-20-1 belongs to indole-building-block, auxiliary class Indoline,Chloride,Sulfonyl chlorides,Amide, name is 1-Methyl-2-oxoindoline-5-sulfonyl chloride, and the molecular formula is C9H8ClNO3S, Product Details of C9H8ClNO3S.

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

Wu, Cheng-Jun published the artcileDesign, synthesis and biological evaluation of indole-based [1,2,4]triazolo[4,3-a] pyridine derivatives as novel microtubule polymerization inhibitors, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is European Journal of Medicinal Chemistry (2021), 113629, database is CAplus and MEDLINE.

A series of indole-based [1,2,4]triazolo [4,3-a]pyridine derivatives was designed and synthesized as novel microtubulin polymerization inhibitors by using a conformational restriction strategy. These compounds exhibited moderate to potent anti-proliferative activities against a panel of cancer cell lines (HeLa, A549, MCF-7 and HCT116). Among them, compound I featuring a N-methyl-5-indolyl substituent at the C-6 position of the [1,2,4]triazolo [4,3-a]pyridine core exhibited the highest antiproliferative activity with the IC₅₀ values ranging from 15 to 69 nM, and remarkable inhibitory effect on tubulin polymerization with an IC₅₀ value of 1.64μM. Mechanistic studies revealed that compound I induced cellular apoptosis and cell cycle arrest at the G₂/M phase in a dose-dependent fashion. Moreover, compound I significantly suppressed wound closure and disturbed microtubule networks.

European Journal of Medicinal Chemistry published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H10O4, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

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

Prieto, Monica published the artcileArylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles. Partner role swapping and heterocycle protection, HPLC of Formula: 642494-36-8, the publication is Journal of Organic Chemistry (2004), 69(20), 6812-6820, database is CAplus and MEDLINE.

Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with Ph bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl, e.g., I. Furthermore, irresp. of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups were essential to ensuring optimum results in these Suzuki couplings.

Journal of Organic Chemistry published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, HPLC of Formula: 642494-36-8.

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

Melzer, Marvin S. published the artcileApplicability of the Hammett equation to the indole system: acidity of indole-3-carboxylic acids, SDS of cas: 10242-03-2, the publication is Journal of Organic Chemistry (1962), 496-9, database is CAplus.

The acidities of six 5- and 6-substituted indole-3-carboxylic acids were determined in aqueous alc. and their pK plotted against the Hammett substituent constants of the resp. substituents. A good correlation was obtained using the one-term Hammett equation (log K/K° = ρσ) using σ_m for groups in the 5-position and σ_p for groups in the 6-position. These results were taken to indicate thai electronic effects were transmitted to the acid center through the C pare to the 6-position and that virtually no transmission occurred through the indole N atom. It was also found that the 5-bromoindole-3-carboxylic acid (I) was somewhat less acidic than expected, an effect attributed to steric and electronic factors. Infrared data indicated that whereas the 6-aminoindole-3-carboxylic acid (II) existed as the free acid, the 5-amino isomer (III) existed in its zwitterionic form. All pK measurements were made in 50% and 95% alc. and the pH measured using a Beckmann meter. Indole treated with MeMgI then CO₂ gave indote-3-carboxylic acid (IV), m. 214° (decomposition). 5-Nitroindote (.5 g.) treated 1 day in a refrigerator with excess (COCl)₂ gave 5 g. 5-nitroindole-3-glyoxylyl chloride (V), m. 310° (decomposition). V refluxed with KOH gave 3.5 g. 5-nitroindole 3-carboxylic acid (VI), m. 270-2° (decomposition). VI (3.5 g.) refluxed 3 hrs. in refluxing 30% H₂O₂, filtered hot, and the solid further purified gave 2.5 g. 5-nitroindole-3-carboxylic acid (VII), m. 276-8° (decomposition). A portion of V treated directly with 30% H₂O₂ gave 47% VII. V failed to undergo decarboxylation in refluxing tetrachloroethane. VII failed to undergo cleavage on treatment with Pb(OAc)₄ in refluxing AcOH. 5-Bromoindole treated with MeMgl and carbonated gave I, m. 238-40° (decomposition). IV in AcOH treated with HNO₃ gave 6-nitroimtole-3-carboxylic acid (VIII), m. 280-1°. Reduction of VIII in MeOH with Raney Ni under 35 lb./sq. in. H pressure gave II. Another preparation using the same procedure gave a small amount of material, m. 197-9°. VI (500 mg.) in MeOH shaken 8 hrs. with Raney Ni under 50 lb./sq. in. H pressure gave 65 mg. III, m. 177-9° (decomposition). The pK of indole-3-carboxylic acids at 26° were obtained (compound, pK in 50% alc., number of determinations, pK in 95% alc., no of determinations, a used, NH (cm.^-1 given): IV, 7.00, 9, 8.92, 3, 0.00, 3247; VIII, 6.45, 3, 8.06, 2, 0.78, 8425; VI, 6.50, 6, 8.15, 3, 0.71, 3338; I, 6.96, 7, 8.72, 3, 0.391, 3310; 5-ethoxyindote-3-carboxylic acid, 6.98, 6, 8.91, 2, 0.10, 3226; II, 7.43, 2, -, -, -0.66, 3312. Reaction constants and precision of correlation of pK of indole-3-carboxylic acids with Hammett substituent constants were given in a table.

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, SDS of cas: 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

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 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

Remers, William A. published the artcileSynthesis of indoles from 4-oxo-4,5,6,7-tetrahydroindoles. III. Introduction of substituents by electrophilic substitution, Recommanded Product: 2-Bromo-6,7-dihydro-1H-indol-4(5H)-one, the publication is Journal of Organic Chemistry (1971), 36(9), 1241-7, database is CAplus.

The general method of indole synthesis by way of 4-oxo-4,5,6,7-tetrahydroindoles (I) was extended by a variety of electrophilic substitution reactions, including bromination, nitration, acylation, and formylation. An order of selective substitution was established as follows: C-2 > C-3 > C-5, except in certain Vilsmeier-Haack formylations of 2-substituted compounds. When the pyrrole ring of a I was substituted with a strong electron-withdrawing group, electrophilic substitution was diverted to C-5. Most of the 6,7-dihydroindoles prepared in this investigation could be dehydrogenated to the fully aromatic indoles, but many of the new I were resistant to dehydrogenation. Vilsmeier-Haack formylation of certain I led directly to fully aromatic indoles which had a 4-chloro-5-(dimethylaminomethyl) pattern of substitution.

Journal of Organic Chemistry published new progress about 27784-79-8. 27784-79-8 belongs to indole-building-block, auxiliary class Other Aromatic Heterocyclic,Bromide,Ketone, name is 2-Bromo-6,7-dihydro-1H-indol-4(5H)-one, and the molecular formula is C8H8BrNO, Recommanded Product: 2-Bromo-6,7-dihydro-1H-indol-4(5H)-one.

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

Appukkuttan, Prasad published the artcileMicrowave enhanced formation of electron rich arylboronates, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Synlett (2003), 1204-1206, database is CAplus.

Microwave assisted synthesis of electron rich aminoaryl- and indolylboronates via palladium-catalyzed boronation of the corresponding aryl bromides with bis(pinacolato)diboron are described. Reaction of bis(pinacolato)diboron with 1-bromo-2-R-4-R¹-benzene catalyzed by Pd(dppf)Cl₂ gave under microwave irradiation 2-(2-R-4-R¹-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes (2a–c, R, R¹: H, NMe₂;, H, NH₂;, NH₂, H). Similar reaction of bromo-1H-indoles XC₈H₆N (5a–d, X = 4-Br, 5-Br, 6-Br, 7-Br) gave the corresponding indolyldioxaborolanes (6a–d). Borylation of tris(4-bromophenyl)amine (3) gave tris[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (4). Compared to conventional heating conditions, dramatic rate enhancements were found for reactions carried out under microwave irradiation, reducing reaction times from hours or days to only minutes.

Synlett published new progress about 642494-36-8. 642494-36-8 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Indole,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C14H18BNO2, Application of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

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