Month: February 2023

Effect of heterocyclic ring system on formation of dimeric quinolones under catalyst-free conditions: a green approach was written by Madhu, Bandi;Raja sekar, B.;Venkata Ramana Reddy, C. H.;Dubey, P. K.. And the article was included in Research on Chemical Intermediates in 2017.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The intermediate-dependent green and efficient synthesis of dimeric quinolones I (R¹ = Me, Et; R² = H, Me, OMe, Cl, Br, NO₂) and II (R³ = Me, Et; R⁴ = Ph, 3-ClC₆H₄, 3,4-(OMe)₂, etc.) was described. Compounds I were prepared by either the Knoevenagel condensation of 4-hydroxy-quinolin-2(1H)-ones with indole-3-carboxaldehydes in water followed by Michael-type addition of the (3-indolylmethylene)quinoline diones under catalyst-free conditions with another equivalent of indole-3-carboxaldehyde or via a one-pot reaction using two equivalent of the aldehyde. Compounds II were prepared by the tandem one-pot Knoevenagel condensation followed by Michael-type addition of 4-hydroxy-quinolin-2(1H)-ones with aromatic aldehydes in water. This reaction was found to be environmentally friendly, has easy-workup and shorter reaction times giving good yields of the product without the need for its isolation using column chromatog. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Quality Control of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Quality Control of 5-Chloroindole-3-carboxaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Highly convenient and large scale synthesis of 5-chloroindole and its 3-substituted analogues was written by Keetha, Laxminarayana;Palle, Sadanandam;Ramanatham, Vinodkumar;Khagga, Mukkanti;Chinnapillai, Rajendiran. And the article was included in Journal of the Korean Chemical Society in 2011.Synthetic Route of C9H5BrN2 This article mentions the following:

A large scale and com. feasible synthesis of 5-chloroindole and its 3-substituted analogs was described via a halogen-halogen exchange reaction from 5-bromoindole and its derivatives using cuprous chloride and dipolar aprotic solvent N-methyl-2-pyrrolidone in one-pot with good yields. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6Synthetic Route of C9H5BrN2).

5-Bromo-3-cyanoindole (cas: 90271-86-6) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Synthetic Route of C9H5BrN2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Fluorogenic Labeling of 5-Formylpyrimidine Nucleotides in DNA and RNA was written by Samanta, Biswajit;Seikowski, Jan;Hoebartner, Claudia. And the article was included in Angewandte Chemie, International Edition in 2016.Application In Synthesis of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate This article mentions the following:

5-Formylcytosine (5fC) and 5-formyluracil (5fU) are natural nucleobase modifications that were generated by oxidative modification of 5-methylcytosine and thymine (or 5-methyluracil). Herein, the authors describe chemoselective labeling of 5-formylpyrimidine nucleotides in DNA and RNA by fluorogenic aldol-type condensation reactions with 2,3,3-trimethylindole derivatives Mild and specific reaction conditions were developed for 5fU and 5fC to produce hemicyanine-like chromophores with distinct photophys. properties. Residue-specific detection was established by fluorescence readout as well as primer-extension assays. The reactions were optimized on DNA oligonucleotides and were equally suitable for the modification of 5fU- and 5fC-modified RNA. This direct labeling approach of 5-formylpyrimidines is expected to help in elucidating the occurrence, enzymic transformations, and functional roles of these epigenetic/epitranscriptomic nucleobase modifications in DNA and RNA. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Application In Synthesis of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application In Synthesis of 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Flame-resisting wool with halo-organic compounds. Part I: Water-soluble or emulsifiable bromine derivatives incorporating one or more reactive centers was written by Thorsen, W. J.. And the article was included in Textile Research Journal in 1976.Reference of 24407-32-7 This article mentions the following:

The flame retardancy of aromatic compounds having Br incorporated with SO3H groups and other reactive sites increased as the acidic nature of the mol. increased. 2,4,6-Tribromometanilic acid [58585-89-0] and tetrabromophthalic acid [13810-83-8], although not washfast, were the most promising; the former was capable of fireproofing wool which had been made shrink-resistant by ozone. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Reference of 24407-32-7).

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 24407-32-7

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

The Synthesis of Sulfinylphthalimides and their Reactions with Some Nucleophiles in Dioxane was written by Bozkurt, Yasemin Soydas;Kutuk, Halil. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2011.HPLC of Formula: 14204-27-4 This article mentions the following:

In this study, some N-(p-substituted-arylsulfinyl)phthalimides (1a-1e) were synthesized. The synthesized compounds were examined with respect to their substitution reactions with sodium ethoxide, sodium methoxide, methylamine, and t-butylamine in dioxane. The substituent effect was investigated at 30.0 ± 0.1 °C. The activation entropy was also studied, and neg. ΔS^{â‰?/sup> values were obtained. Configuration inversions were observed in the substitution reactions. This result is in conformity with the S_N2 mechanism. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4HPLC of Formula: 14204-27-4).}

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.HPLC of Formula: 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Analogs of the Dopamine Metabolite 5,6-Dihydroxyindole Bind Directly to and Activate the Nuclear Receptor Nurr1 was written by Kholodar, Svetlana A.;Lang, Geoffrey;Cortopassi, Wilian A.;Iizuka, Yoshie;Brah, Harman S.;Jacobson, Matthew P.;England, Pamela M.. And the article was included in ACS Chemical Biology in 2021.Reference of 4769-96-4 This article mentions the following:

The nuclear receptor-related 1 protein, Nurr1, is a transcription factor critical for the development and maintenance of dopamine-producing neurons in the substantia nigra pars compacta, a cell population that progressively loses the ability to make dopamine and degenerates in Parkinson’s disease. Recently, we demonstrated that Nurr1 binds directly to and is regulated by the endogenous dopamine metabolite 5,6-dihydroxyindole (DHI). Unfortunately, DHI is an unstable compound, and thus a poor tool for studying Nurr1 function. Here, we report that 5-chloroindole, an unreactive analog of DHI, binds directly to the Nurr1 ligand binding domain with micromolar affinity and stimulates the activity of Nurr1, including the transcription of genes governing the synthesis and packaging of dopamine. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Reference of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Reference of 4769-96-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

An investigation into the substituent effect of halogen atoms on the crystal structures of indole-3-carboxylic acid (ICA) was written by Luo, Yang-Hui;Sun, Bai-Wang. And the article was included in CrystEngComm in 2013.Electric Literature of C9H6ClNO This article mentions the following:

A study into the substituent effect of halogen atoms (F, Cl, Br) on the crystal structure of indole-3-carboxylic acid (ICA) was prepared The study was done through the aspect of crystal structure, intermol. interactions and π···π stacking motifs with the assistance of IR spectra, elemental analyses, NMR spectra, DSC, thermogravimetric analyses (TGA) and hot stage microscopy (HSM) measurements. The different kinds of halogen atoms and the different substituted positions have a significant effect on the crystal structures, mol. π···π stacking motifs and the kinds of intermol. interactions. The authors further correlated the m.ps. of the ICAs with the H-H, O-H and X-H (X = F, Cl, Br) interactions, and found a pos. correlation between them. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Electric Literature of C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Electric Literature of C9H6ClNO

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis and screening of 3-(4-oxo-2-phenyl-1,3-thiazol-5(4H)-ylidene)-1,3-dihydro-2H-indol-2-one-N-methylanilines for antiinflammatory activity was written by Devi, N. Saritha;Srinivas, B.;Sarangapani, Manda. And the article was included in Journal of Pharmaceutical Sciences and Research in 2019.Name: 7-Nitroindoline-2,3-dione This article mentions the following:

A novel 3-(4-oxo-2-phenyl-1,3-thiazol-5(4H)-ylidene)-1,3-dihydro-2H-indol-2-one -N-methylaniline derivatives I [R = 5-Cl, 7-Me, 5,6-di-Cl, etc.] was synthesized by cyclization of isatins with thiazolidinone. The compounds I [R = 5-F, 5-Cl, 7-Cl, 5-Br, 5,6-di-Cl, 5-OH] were evaluated for in vivo antiinflammatory activity. The compound I [R = 5,6-di-Cl] showed more in vivo antiinflammatory activity with 72.5% of inhibition among test compounds The compound I [R = 5-F, 5-Cl, 7-Cl, 5-Br, 5-OH] were next in the order of exhibiting in vivo antiinflammatory activity with 65.75, 63.0, 52.5, 61.25 and 51.25 % resp., when compared to standard drug Indomethacin with 73.7% of inhibition. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Name: 7-Nitroindoline-2,3-dione).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Name: 7-Nitroindoline-2,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Design, synthesis and biological evaluation of novel hybrids targeting mTOR and HDACs for potential treatment of hepatocellular carcinoma was written by Zhai, Shiyang;Zhang, Huimin;Chen, Rui;Wu, Jiangxia;Ai, Daiqiao;Tao, Shunming;Cai, Yike;Zhang, Ji-Quan;Wang, Ling. And the article was included in European Journal of Medicinal Chemistry in 2021.Related Products of 754214-56-7 This article mentions the following:

Hepatocellular carcinoma (HCC) is a major contributor to global cancer incidence and mortality. Many pathways are involved in the development of HCC and various proteins including mTOR and HDACs have been identified as potential drug targets for HCC treatment. In the present study, two series of novel hybrid mols. targeting mTOR and HDACs were designed and synthesized based on parent inhibitors (MLN0128 and PP121 for mTOR, SAHA for HDACs) by using a fusion-type mol. hybridization strategy. In vitro antiproliferative assays demonstrated that these novel hybrids with suitable linker lengths exhibited broad cytotoxicity against various cancer cell lines, with significant activity against HepG2 cells. Notably, DI06, an MLN0128-based hybrid, exhibited antiproliferative activity against HepG2 cells with an IC50 value of 1.61μM, which was comparable to those of both parent drugs (MLN0128, IC50 = 2.13μM and SAHA, IC50 = 2.26μM). In vitro enzyme inhibition assays indicated that DI06, DI07 and DI17 (PP121-based hybrid) exhibited nanomolar inhibitory activity against mTOR kinase and HDACs (e.g., HDAC1, HDAC2, HDAC3, HADC6 and HADC8). Cellular studies and western blot analyses uncovered that in HepG2 cells, DI06 and DI17 induced cell apoptosis by targeting mTOR and HDACs, blocked the cell cycle at the G0/G1 phase and suppressed cell migration. The potential binding modes of the hybrids (DI06 and DI17) with mTOR and HDACs were investigated by mol. docking. DI06 displayed better stability in rat liver microsomes than DI07 and DI17. Collectively, DI06 as a novel mTOR and HDACs inhibitor presented here warrants further investigation as a potential treatment of HCC. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Related Products of 754214-56-7).

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Related Products of 754214-56-7

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes was written by Huang, Chunhui;Chernyak, Natalia;Dudnik, Alexander S.;Gevorgyan, Vladimir. And the article was included in Advanced Synthesis & Catalysis in 2011.Computed Properties of C10H10BrN This article mentions the following:

A novel, easily removable and modifiable silicon-tethered pyridyldiisopropylsilyl directing group for C-H functionalizations of arenes has been developed. The installation of the pyridyldiisopropylsilyl group can efficiently be achieved via two complementary routes using easily available 2-(diisopropylsilyl)pyridine (I). The first strategy features a nucleophilic hydride substitution at the silicon atom in I with aryllithium reagents generated in situ from the corresponding aryl bromides or iodides. The second milder route exploits a highly efficient room-temperature rhodium(I)-catalyzed cross-coupling reaction between I and aryl iodides. The latter approach can be applied to the preparation of a wide range of pyridyldiisopropylsilyl-substituted arenes possessing a variety of functional groups, including those incompatible with organometallic reagents. The pyridyldiisopropylsilyl directing group allows for a highly efficient, regioselective palladium(II)-catalyzed mono-ortho-acyloxylation and ortho-halogenation of various aromatic compounds Most importantly, the silicon-tethered directing group in both acyloxylated and halogenated products can easily be removed or efficiently converted into an array of other valuable functionalities. These transformations include protio-, deuterio-, halo-, boro-, and alkynyldesilylations, as well as a conversion of the directing group into the hydroxy functionality. In addition, the construction of aryl-aryl bonds via the Hiyama-Denmark cross-coupling reaction is feasible for the acetoxylated products. Moreover, the ortho-halogenated pyridyldiisopropylsilylarenes, bearing both nucleophilic pyridyldiisopropylsilyl and electrophilic aryl halide moieties, represent synthetically attractive 1,2-ambiphiles. A unique reactivity of these ambiphiles has been demonstrated in efficient syntheses of arylenediyne and benzosilole derivatives, as well as in a facile generation of benzyne. In addition, preliminary mechanistic studies of the acyloxylation and halogenation reactions have been performed. A trinuclear palladacycle intermediate has been isolated from a stoichiometric reaction between diisopropyl(phenyl)pyrid-2-ylsilane and palladium acetate. Furthermore, both C-H functionalization reactions exhibited equally high values of the intramol. primary kinetic isotope effect (k_H/k_D = 6.7). Based on these observations, a general mechanism involving the formation of a palladacycle via a C-H activation process as the rate-determining step has been proposed. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Computed Properties of C10H10BrN).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Computed Properties of C10H10BrN

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles