Month: January 2023

Synthesis, antiproliferative and antimalarial activities of dinuclear silver(I) complexes with triphenylphosphine and thiosemicarbazones ligands was written by Khir, Nur Adila Fatin Mohd;Abd Razak, Mohd Ridzuan Mohd;Nordin, Fariza Juliana;Sofyan, Nur Rahimah Fitrah Mohd;Rajab, Nor Fadilah;Sarip, Rozie. And the article was included in Indonesian Journal of Chemistry in 2021.SDS of cas: 827-01-0 This article mentions the following:

A series of six sulfur-bridged dinuclear silver(I) thiosemicarbazone complexes were synthesized through the reaction of silver(I) nitrate with 4-phenyl-3- thiosemicarbazone derivatives together with triphenylphosphine (PPh₃) (in a 1:1:2 molar ratio). Following structural characterizations using various techniques such as elemental anal., Fourier-transform IR (FTIR) spectroscopy, as well as ¹H, ¹³C, ³¹P{¹H}s, COSY and ¹H-¹³C NMR spectroscopy, it was found that the thiosemicarbazone ligand exists in the form of a thione rather than thiol tautomer. Subsequently, MDA-MB-231 and MCF-7 breast cancer cell lines, as well as the HT-29 colon cancer cell lines, were used to investigate the in-vitro antiproliferative activities of these complexes. In all cases, the IC₅₀ values were in the potent micromolar range. Besides, the aforementioned complexes also had good antiplasmodial activity against chloroquine-resistant P. falciparum, as per the results of histidine-rich protein 2 (HRP2) assays and cytotoxicity evaluations of MDBK cells. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0SDS of cas: 827-01-0).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.SDS of cas: 827-01-0

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

Use of formic acid as a cyclization agent in the synthesis of indoles by the Fischer method was written by Kidwai, Akhlaq R.;Khan, Naseem H.. And the article was included in Compt. Rend. in 1963.Safety of 3-(1H-Indol-1-yl)propanoic acid This article mentions the following:

Indoles have been prepared by cyclization of simple or substituted phenylhydrazones of aldehydes, ketones, or ketonic acids by ZnCl₂, BF₃, H₂SO₄, AcOH, polyphosphoric acid, aqueous AcOH or HCl, or EtOH-HCl. HCO₂H (I) was also found to be a suitable cyclization agent. II (R = Ph, R’ = H, P” = CO₂H) (1 g.) in 40 ml. 50% I refluxed 4 hrs., evaporated in vacuo on a H₂O bath, the residue dissolved in H₂O, the solution extracted with Et₂O, the extract washed with aqueous NaHCO₃, the combined alk. solutions treated with C, and acidified gave 91% III (R = Ph, R’ = H, R” = CO₂H), m. 186° (EtOH). Similarly were prepared, from II (R = Ph, R’ = NO₂, R” = CO₂H), 70% III (R = Ph, R’ = NO₂, R” = CO₂H) (IV), m. 247.5° (EtOH-H₂O), and from II [R = CH₂C(NHAc)(CO₂Et)₂, R’ = R” = H], 63% III [R = CH₂C(NHAc)(CO₂Et)₂, R’ = R” = H], m. 158° (C₆H₆-petr. ether). Whether the NO₂ group in IV was in the 4- or 6-position was undetermined In the case of IV, the product was isolated directly from the Et₂O solution Neg. results were obtained with the phenylhydrazones of AcCO₂H and AcH, which could not be cyclized with the other above-cited cyclization agents. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Safety of 3-(1H-Indol-1-yl)propanoic acid).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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). Safety of 3-(1H-Indol-1-yl)propanoic acid

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 characterization of new isatin derivatives for cytototoxic activity was written by Shoba, Rani B.;Blessi, Priyanka K.;Gade, Sammaiah. And the article was included in International Journal of Pharmacy and Biological Sciences in 2015.Synthetic Route of C8H4N2O4 This article mentions the following:

A series of N-(6-benzoyl-1H-benzo[d]imidazol-2-yl)-2-(2-oxoindolin-3-ylidene) hydrazine carboxamides were synthesized by treating (5-benzoyl-1H-benzo[d]imidazol-2-yl) carbamate with different substituted isatins. The novel compounds were characterized on the basis of spectral (FT-IR, 1H NMR, Mass) anal. All the synthesized derivatives were screened for cytotoxic activity against Hela cancer cell lines using MTT assay. All the synthesized compounds produced a dose dependent inhibition of growth of the cells. The IC50 values of all the synthetic test compounds were found between 17.32-55.57. The potency of (IC50 values) of cytotoxic activity of compounds was compared with that of known cytotoxic agent, Cisplatin. Almost all the synthesized novel compounds showed the most potent activity against all cell lines. These results indicate that C-5 substituted derivatives may be useful leads for anticancer drug development in future. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Synthetic Route of C8H4N2O4

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 of new fireproofing agents for fibers. 1 was written by Sumi, Koichi. And the article was included in Osaka-furitsu Sen’i Gijutsu Kenkyusho Kenkyu Hokoku in 1978.Electric Literature of C8HBr4NO2 This article mentions the following:

2,4-Bis(tetrahalophthalimido)-6-chloro-s-triazines I, where R is Cl or Br, were prepared and were useful as fireproofing agents for textiles. For example, 1.78 mol formamide [75-12-7] was treated with 0.07 mol tetrachlorophthalic anhydride [117-08-8], 0.035 mol of the resulting tetrachlorophthalimide [1571-13-7] was treated with 0.035 mol KOH, and 0.0334 mol of the K salt [59653-19-9] was treated with 0.0167 mol. cyanuric chloride [108-77-0] to give I (R = Cl) [73341-50-1]. In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7Electric Literature of C8HBr4NO2).

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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). Electric Literature of C8HBr4NO2

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 SAR of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-1 was written by Marcin, Lawrence R.;Higgins, Mendi A.;Zusi, F. Christopher;Zhang, Yunhui;Dee, Michael F.;Parker, Michael F.;Muckelbauer, Jodi K.;Camac, Daniel M.;Morin, Paul E.;Ramamurthy, Vidhyashankar;Tebben, Andrew J.;Lentz, Kimberley A.;Grace, James E.;Marcinkeviciene, Jovita A.;Kopcho, Lisa M.;Burton, Catherine R.;Barten, Donna M.;Toyn, Jeremy H.;Meredith, Jere E.;Albright, Charles F.;Bronson, Joanne J.;Macor, John E.;Thompson, Lorin A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Formula: C9H6ClNO This article mentions the following:

Heterocyclic replacement of the isophthalamide Ph ring in hydroxyethylamine (HEA) BACE-1 inhibitors was explored. A variety of indole-1,3-dicarboxamide HEAs I (X = CH; R¹ = R² = Et, n-Pr, n-Bu; R¹ = n-Bu, R² = H, Me; R³ = H, F, CN; R⁴ = H, F, Cl, CF₃, CO₂H, etc.; R⁵ = 3-MeOC₆H₄CH₂; R⁶ = H, F) exhibited potent BACE-1 enzyme inhibition, but displayed poor cellular activity. Improvements in cellular activity and aspartic protease selectivity were observed for 7-azaindole-1,3-dicarboxamide HEAs I (X = N; R¹ = Bu, n-pentyl, isopentyl, MeOCH₂CH₂, R² = Me; R¹ = cyclopropylmethyl, R² = n-Pr; R¹R²N = 2-ethoxymethyl-1-piperidinyl, etc.; R³ = R⁴ = H; R⁵ = 3-MeOC₆H₄CH₂, 3-MeOC₆H₄CO, cyclopropyl, etc.; R⁶ = H, F). A methylprolinol-bearing azaindole I [X = N; R¹R²N = (R)-2-methoxymethyl-1-pyrrolidinyl; R³ = R⁴ = H; R⁵ = 3-MeOC₆H₄CH₂; R⁶ = F] demonstrated robust reductions in rat plasma Aβ levels, but did not lower rat brain Aβ due to poor central exposure. The same compound exhibited a high efflux ratio in a bidirectional Caco-2 assay and was likely a substrate of the efflux transporter P-glycoprotein. X-ray crystal structures are reported for two indole HEAs in complex with BACE-1. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Formula: C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Formula: 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

Substrate multiplexed protein engineering facilitates promiscuous biocatalytic synthesis was written by McDonald, Allwin D.;Higgins, Peyton M.;Buller, Andrew R.. And the article was included in Nature Communications in 2022.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

Enzymes with high activity are readily produced through protein engineering, but intentionally and efficiently engineering enzymes for an expanded substrate scope is a contemporary challenge. One approach to address this challenge is Substrate Multiplexed Screening (SUMS), where enzyme activity is measured on competing substrates. SUMS has long been used to rigorously quantitate native enzyme specificity, primarily for in vivo settings. SUMS has more recently found sporadic use as a protein engineering approach but has not been widely adopted by the field, despite its potential utility. Here, we develop principles of how to design and interpret SUMS assays to guide protein engineering. This rich information enables improving activity with multiple substrates simultaneously, identifies enzyme variants with altered scope, and indicates potential mutational hot-spots as sites for further engineering. These advances leverage common laboratory equipment and represent a highly accessible and customizable method for enzyme engineering. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Recommanded Product: 6-Nitro-1H-indole

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

L-Proline/K₂CO₃-Catalyzed Eco-friendly Synthesis of Novel 2-(1H-Indol-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one Derivatives was written by Hari Krishna Reddy, V.;Prashanth Reddy, G.;Krishna Mohan, T.;Venkateswara Rao, A.. And the article was included in Russian Journal of Organic Chemistry in 2021.Quality Control of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Abstract: A green and eco-friendly synthesis of novel 2-(1H-indol-3-yl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives have been developed using L-proline as a simple catalyst. Two efficient methods have been described for the synthesis of dihydroquinazolin-4(1H)-one derivatives In the first method, 1H-1,3-benzoxazine-2,4-dione reacted with substituted anilines and 1H-indole-3-carbaldehydes in water in the presence of L-proline as a catalyst, whereas in the second method, a similar reaction using 1H-indol-3-ylmethanol instead of indole-3-carbaldehyde was catalyzed by L-proline/K₂CO₃ at room temperature for 30 min to afford the same products. These two protocols involve eco-friendly and inexpensive catalysts and produce the target products in excellent yields with a sufficient purity, so that there was no need of column chromatog. for their isolation or purification 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, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.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

2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic Acid (PSI-697): Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists was written by Kaila, Neelu;Janz, Kristin;Huang, Adrian;Moretto, Alessandro;DeBernardo, Silvano;Bedard, Patricia W.;Tam, Steve;Clerin, Valerie;Keith, James C. Jr.;Tsao, Desiree H. H.;Sushkova, Natalia;Shaw, Gray D.;Camphausen, Raymond T.;Schaub, Robert G.;Wang, Qin. And the article was included in Journal of Medicinal Chemistry in 2007.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small mol. P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clin. development for the treatment of atherothrombotic vascular events. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Name: 2-(5-Chloro-1H-indol-3-yl)acetic acid

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

Discovery of Indolone Acetamides as Novel SV2A Ligands with Improved Potency Toward Seizure Suppression was written by Frycia, Anne;Starck, Jean-Philippe;Jadot, Sophie;Lallemand, Benedicte;Leclercq, Karine;Lo Brutto, Patrick;Matagne, Alain;Verbois, Valerie;Mercier, Joel;Kenda, Benoit. And the article was included in ChemMedChem in 2010.Synthetic Route of C11H11NO2 This article mentions the following:

Capitalizing on the proven clin. efficacy of levetiracetam (I) as an antiepileptic drug, a drug discovery program led to the identification of a new generation of SV2A ligands with equal or better tolerability profiles than levetiracetam, and improved potency toward seizure suppression in animal models. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Synthetic Route of C11H11NO2).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C11H11NO2

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

Green synthesis of new pyrrolidine-fused spirooxindoles via three-component domino reaction in EtOH/H₂O was written by Wang, Yong-Chao;Wang, Jun-Liang;Burgess, Kevin S.;Zhang, Jiang-Wei;Zheng, Qiu-Mei;Pu, Ya-Dan;Yan, Li-Jun;Chen, Xue-Bing. And the article was included in RSC Advances in 2018.Name: 5,6-Difluoroindoline-2,3-dione This article mentions the following:

An efficient, green and sustainable approach for the synthesis of novel polycyclic pyrrolidine-fused spirooxindole compounds such as I [R¹ = H, Me; R² = H, Ph; R³ = H, Me; R⁴ = H, 5-Me, 6-Cl, etc.] and II [X = CH₂, S] was developed. The synthesis included a one-pot, three-component, domino reaction of (E)-3-(2-nitrovinyl)-indoles, isatins and chiral polycyclic α-amino acids under catalyst-free conditions at room temperature in EtOH-H₂O. The salient features of this methodol. were eco-friendliness, high yields and the ease of preparation of target compounds I without the involvement of toxic solvents and column chromatog. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Name: 5,6-Difluoroindoline-2,3-dione).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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). Name: 5,6-Difluoroindoline-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