Day: February 20, 2023

Synthesis of a 3′-C-ethynyl-闁?D-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides was written by Hulpia, Fabian;Noppen, Sam;Schols, Dominique;Andrei, Graciela;Snoeck, Robert;Liekens, Sandra;Vervaeke, Peter;Van Calenbergh, Serge. And the article was included in European Journal of Medicinal Chemistry in 2018.Name: 3-Bromo-4-chloro-7-azaindole This article mentions the following:

A focused nucleoside library was constructed around a 3′-C-ethynyl-D-ribofuranose sugar scaffold, which was coupled to variously modified purine nucleobases. The resulting nucleosides were probed for their ability to inhibit tumor cell proliferation, as well as for their activity against a panel of relevant human viruses. While C6-aryl substituted purine nucleosides were found to be weakly active, several C7-substituted 7-deazapurine nucleosides elicited potent antiproliferative activity. Their activity spectrum was evaluated in the NCI-60 tumor cell line panel indicating activity against several solid tumor derived cell lines. Analog I, equipped with a 7-deaza 7-chloro-6-amino-purin-9-yl base was evaluated in a metastatic breast tumor (MDA-MB-231-LM2) xenograft model. It inhibited both tumor growth and reduced the formation of lung metastases as revealed by BLI anal. The dideazanucleoside analog II showed interesting activity against hCMV. These results highlight the potential advantages of recombining known sugar and nucleobase motifs as a library design strategy to discover novel antiviral or antitumor agents. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Name: 3-Bromo-4-chloro-7-azaindole).

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: 3-Bromo-4-chloro-7-azaindole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Cyclocondensation reactions of heterocyclic carbonyl compounds. I. Synthesis of some 6-substituted 2,3-dihydro-5H-1,2,4-triazino[5,6-b]indole-3-thiones was written by Hlavac, Jan;Slouka, Jan. And the article was included in Acta Universitatis Palackianae Olomucensis, Facultas Rerum Naturalium in 1993.Category: indole-building-block This article mentions the following:

Condensation of 7-nitroisatin and 7-methylisatin with thiosemicarbazide in acetic acid gave the corresponding 闁?thiosemicarbazones. These 闁?thiosemicarbazones were converted into 1,2,4-triazino[6,5-b]indole-3-thiones I (R = NO₂, Me). In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Category: indole-building-block).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 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 N-(2, 4-dioxo-1, 2-dihydro-3H-spiro [indole-3, 2-[1,3]thiazolidin]-3-yl)-2-hydroxybenzamides for anti-bacterial activity was written by Devi, N. Saritha;Srinivas, B.;Sarangapani, Manda. And the article was included in International Journal of Pharmaceutical Sciences and Research in 2019.Name: 7-Nitroindoline-2,3-dione This article mentions the following:

A novel synthesis of N-(2, 4-dioxo-1, 2-dihydro-3H-spiro [indole-3, 2-[1, 3] thiazolidin]-3-yl)-2-hydroxybenzamide derivatives were synthesized by cyclization of isatin hydrazones with thioglycolic acid. The synthesized compounds were characterized by spectral data (IR, 1H-NMR, Mass) and evaluated for antibacterial activity against various strains of bacteria at the concentrations of 200濠电偞鎸鹃幐?mL. Among the tested compounds X(i) is highly active against E. coli, X(f) is active against B. subtilis, X(h) is active against S. aureus and X(c) is active against S. typhi. 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 produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Name: 7-Nitroindoline-2,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of 1-(3-aminopropyl)indoles and 3-indol-1-ylpropionic acids was written by Basanagoudar, L. D.;Siddappa, S.. And the article was included in Journal of the Chemical Society [Section] C: Organic in 1967.Synthetic Route of C11H11NO2 This article mentions the following:

Various substituted indoles and their derivatives were condensed with acrylonitrile in the presence of trimethylbenzylammonium hydroxide to give the corresponding 3-indol-1-ylpropionitriles. These nitriles were reduced catalytically with Raney nickel to the corresponding 1-(3-aminopropyl)indoles, or hydrolyzed to the corresponding 3-indol-1-ylpropionic acids. Some of the nitriles were formylated to give the corresponding 1-(2-cyanoethyl)indole-3-carboxaldehydes. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Synthetic Route of C11H11NO2).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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.Synthetic Route of C11H11NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of Quinoline-4-carboxamides and Quinoline-4-carboxylates via a Modified Pfitzinger Reaction of N-Vinylisatins was written by Mijangos, Marco V.;Amador-Sanchez, Yoarhy A.;Miranda, Luis D.. And the article was included in European Journal of Organic Chemistry in 2021.Recommanded Product: 150560-58-0 This article mentions the following:

A synthetic approach for the accelerated assembly of quinoline-4-carboxamide and quinoline-4-carboxylate nuclei is presented. The methodol. is based on the rearrangement of N-vinylisatins promoted by different types of amines (or ethanol) in a Pfitzinger-type mechanism that, in turn, builds the quinoline ring system. The reaction took place only by heating the starting materials in ethanol, without any additive. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Recommanded Product: 150560-58-0).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Recommanded Product: 150560-58-0

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of 3-indoleacetic acids and 2-carboxy-3-indoleacetic acids with substituents in the benzene ring was written by Fox, Sidney W.;Bullock, Milon W.. And the article was included in Journal of the American Chemical Society in 1951.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Preceding abstract Cyclization of the corresponding succinaldehydic acid phenylhydrazones yielded the following 3-indoleacetic acid derivatives (m.p. and yield (%) given): 5-Cl, 158-9.5闂?(decomposition), 20; 7-Cl, 164-5闂? 13; 5,7-di-Cl 194-7闂?(decomposition), 9; 5-Me, 151-2闂? 31; 4-Cl, 185-7闂?(decomposition), 19; 6-Cl, 187-8闂?(decomposition), 26; 4- and 6-Cl eutectic mixture, 158-9闂?(decomposition), 16. 2,6-Cl(O₂N)C₆H₄Me (Uhle, C.A. 43, 4255d) yielded 4-chloroindole (I), b₁₃ 150闂? n_D²⁰ 1.6286, d₂₀²⁰ 1.259. I (8.0 g.), 4.3 g. 36% HCHO, 9.3 g. 25% Me₂NH, and 26 cc. AcOH allowed to stand at room temperature overnight, distilled in vacuo, 75 cc. water added, and the mixture filtered and made alk. with N NaOH yielded 8.4 g. 4-chlorogramine (II), m. 147-8.5闂?(150-1闂?when heated fairly rapidly) (from Me₂CO). Attempted conversion of II to 4-chloro-3-indoleacetic acid yielded a small amount of crude acid and an unidentified, higher-melting solid. 4,2-Cl-(O₂N)C₆H₃Me yielded 6-chloro-2-indolecarboxylic acid (III), m. 242-4闂?(decomposition) (from aqueous EtOH). III (8.8 g.) added to 60 cc. tech., anhydrous quinoline containing 5 g. CuCl at 150闂? the mixture heated 3 h. at 240闂?(bath temperature), cooled, triturated with Et₂O, shaken with water, the solid filtered off, washed with dilute HCl and Et₂O, the water-Et₂O mixture acidified with HCl, and the Et₂O distilled yielded 5 g. 6-chloroindole (IV), m. 83.6闂? EtMgI (35 cc. of a 0.033 M solution) added to 5 g. IV in 25 cc. Et₂O, the mixture stirred at ice-bath temperature 1 h., 2.8 g. ClCH₂CN in 25 cc. Et₂O added dropwise, the mixture stirred 30 min. at 0闂? refluxed 4 h., cooled, 3 cc. AcOH in 50 cc. water added, then 50 cc. C₆H₆, the mixture allowed to stand overnight, the aqueous layer extracted with C₆H₆ (solid discarded), the Et₂O-C₆H₆ layer distilled, the residue distilled at 160-80闂?0.2, the distillate refluxed 4 h. with 10 cc. MeOH and 20 cc. 20% aqueous KOH, filtered with C through diatomaceous earth, the filtrate extracted with Et₂O, and the aqueous layer acidified yielded 1.8 g. 6-chloro-3-indoleacetic acid. Cyclization of the 婵?ketoglutaric acid phenylhydrazones obtained as byproducts yielded the following 2-carboxy-3-indoleacetic acids (m.p. (decomposition), and yield (%) given): 7-Cl, 253闂? 31; 5-Me, 243闂? -; 7-Me, 228-9闂? 6; 5-Br, 247-8闂? 13. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Recommanded Product: 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

New Generation of Selective Androgen Receptor Degraders: Our Initial Design, Synthesis, and Biological Evaluation of New Compounds with Enzalutamide-Resistant Prostate Cancer Activity was written by Hwang, Dong-Jin;He, Yali;Ponnusamy, Suriyan;Mohler, Michael L.;Thiyagarajan, Thirumagal;McEwan, Iain J.;Narayanan, Ramesh;Miller, Duane D.. And the article was included in Journal of Medicinal Chemistry in 2019.Electric Literature of C8H6N2O2 This article mentions the following:

In our effort to find small-mol. treatments of advanced prostate cancers (PCs), a novel series of indolyl and indolinyl propanamides (series II and III) were discovered as selective androgen receptor degraders (SARDs). Initial studies of androgen receptor (AR) antagonist (1) and agonist (2) propanamides yielded a tertiary aniline (3) with novel SARD activity but poor metabolic stability. Cyclization to II and III produced submicromolar AR antagonism and protein degradation selective to AR and AR splice variant (AR SV). II and III maintained potency against enzalutamide-resistant (Enz-R) mutant ARs and PC cells and were efficacious in Enz-R xenografts, suggesting their potential to treat advanced PCs. Design, synthesis, and biol. activity of novel SARDs that could potentially be used for the treatment of a wide spectrum of PCs including castration-resistant, Enz-R, and/or AR SV-dependent advanced PCs that are often untreatable with known hormone therapies are discussed. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C8H6N2O2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Palladium-Catalyzed Three-Component Regioselective Dehydrogenative Coupling of Indoles, 2-Methylbut-2-ene, and Carboxylic Acids was written by Zhang, Xing-Long;Guo, Rui-Li;Wang, Meng-Yue;Zhao, Bao-Yin;Jia, Qiong;Yang, Jin-Hui;Wang, Yong-Qiang. And the article was included in Organic Letters in 2021.Product Details of 4769-96-4 This article mentions the following:

An unprecedented palladium-catalyzed three-component dehydrogenative cascade coupling of indoles, 2-methylbut-2-ene, and carboxylic acids or methanol has been developed. The approach enables the straightforward introduction of a C3′-bonded five-carbon structural unit with a tertiary alc. quaternary carbon center giving access to functionalized indoles I (R¹ = H, 5-Me, 6-Br, 6-NO₂, etc.; R² = Me, n-pentyl, Ph, 2-thienyl, etc.; R³ = Me, MeCO, cyclopropylcarbonyl, ClCHMeCO, etc.). The protocol employs 2-methylbut-2-ene as the C5 source and features a broad substrate scope, atom and step economies, and high chemo- and regioselectivies. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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). Product Details of 4769-96-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Novel cyclopropapyrroloindole (CPI) bisalkylators bearing methoxycarbonyl and trifluoromethyl groups was written by Fukuda, Yasumichi;Furuta, Hirosuke;Kusama, Yoshie;Ebisu, Hiroyuki;Oomori, Yasuo;Terashima, Shiro. And the article was included in Bioorganic & Medicinal Chemistry Letters in 1998.Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

Novel 3-(methoxycarbonyl)-2-(trifluoromethyl)cyclopropapyrroloindole (MCTFCPI) bisalkylators were synthesized, and their antitumor activity was evaluated. Among these derivatives, I was found to exhibit more prominent cytotoxicity and antitumor activity than U-77,779 (bizelesin). In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Recommanded Product: Methyl 5-bromo-1H-indole-2-carboxylate

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues was written by Chen, Chou-Hsiung;Genapathy, Sivaneswary;Fischer, Peter M.;Chan, Weng C.. And the article was included in Organic & Biomolecular Chemistry in 2014.Reference of 827-01-0 This article mentions the following:

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogs were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A, and its analogs. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Reference of 827-01-0).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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 827-01-0

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles