Month: January 2023

Synthesis and broad antiviral activity of novel 2-aryl-isoindolin-1-ones towards diverse enterovirus A71 clinical isolates was written by Wang, Yixuan;Wang, Huiqiang;Jiang, Xinbei;Jiang, Zhi;Guo, Tingting;Ji, Xingyue;Li, Yanping;Li, Yuhuan;Li, Zhuorong. And the article was included in Molecules in 2019.Recommanded Product: 2-Phenylisoindolin-1-one This article mentions the following:

Enterovirus 71 (EV-A71) is the main causative pathogen of childhood hand, foot and mouth disease. Effective medicine is currently unavailable for the treatment of this viral disease. Using the fragment-hopping strategy, a series of 2-aryl-isoindolin-1-one compounds were designed, synthesized and investigated for their in vitro antiviral activity towards multiple EV-A71 clin. isolates (H, BrCr, Shenzhen98, Jiangsu52) in Vero cell culture in this study. The structure-activity relationship (SAR) studies identified 2-phenyl-isoindolin-1-ones as a new potent chemotype with potent antiviral activity against EV-A71. Ten out of the 24 tested compounds showed significant antiviral activity (EC50 < 10 muM) towards four EV-A71 strains. Compounds A3 and A4 exhibited broad and potent antiviral activity with the 50% effective concentration (EC50) values in the range of 1.23-1.76 muM. Moreover, the selectivity indexes of A3 and A4 were significantly higher than those of the reference compound, pirodavir. The western blotting experiment indicated that the viral VP1 was significantly decreased at both the protein and RNA level in a dose-dependent manner following treatment with compound A3. Moreover, compound A3 inhibited the viral replication by acting on the virus entry stage. In summary, this study led to the discovery of 2-aryl-isoindolin-1-ones as a promising scaffold with potent anti-EV-A71 activities, which deserves further in-depth studies. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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: 2-Phenylisoindolin-1-one

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

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones was written by Liu, Yonggui;Luo, Guoyong;Yang, Xing;Jiang, Shichun;Xue, Wei;Chi, Yonggui Robin;Jin, Zhichao. And the article was included in Angewandte Chemie, International Edition in 2020.Safety of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

The aromatic nitrogen atoms of heteroarylaldehydes were activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products I [R¹ = H, 8′-Br, 7′-Cl, etc.; R² = H, 4-Br, 5-Cl, etc.; R³ = Me, Bn, Trt], II [R¹ = H, 8-Br, 7-F, etc.; R² = H, 3-Me, 4-Cl, etc.; R³ = Me, Et, Ph, Bn, CHPh₂] and III [R¹ = H, 6;t-Bu, 7’Cl, etc.; R² = H, 4-Cl, 5-Me, etc.] were afforded in good to excellent yields and optical purities. Reaction involved the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibited excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichems. for plant protection. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Safety of 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Safety of 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

Aryne approach towards 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles was written by Kopchuk, Dmitry S.;Nikonov, Igor L.;Zyryanov, Grigory V.;Nosova, Emiliya V.;Kovalev, Igor S.;Slepukhin, Pavel A.;Rusinov, Vladimir L.;Chupakhin, Oleg N.. And the article was included in Mendeleev Communications in 2015.Application of 774-47-0 This article mentions the following:

Reaction between 3-(2-pyridyl)-1,2,4-triazines and in situ generated 4,5-difluorobenzyne in toluene affords 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles. The structure of one representative compound was confirmed by X-ray diffraction anal. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Application of 774-47-0).

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Application of 774-47-0

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

Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}indolin-2-one derivatives was written by Gudipati, Rajyalakshmi;Anreddy, Rama Narsimha Reddy;Manda, Sarangapani. And the article was included in Saudi Pharmaceutical Journal in 2011.Recommanded Product: 112656-95-8 This article mentions the following:

Series of 5- or 7-substituted 3-{4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenylimino}-indolin-2-one derivatives were synthesized by treating 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thiol with different isatin derivatives The newly synthesized compounds were characterized on the basis of spectral (FT-IR, ¹H NMR, MS) analyses. All the synthesized derivatives were screened for anticancer activity against HeLa cancer cell lines using MTT assay. All the synthetic compounds produced a dose dependent inhibition of growth of the cells. The IC₅₀ values of all the synthetic test compounds were found between 10.64 and 33.62 μM. The potency (IC₅₀ values) of anticancer activity of the the halo-substituted compounds was comparable with that of known anticancer agent, Cisplatin. Among the synthesized 2-indolinones, these halo-substituted compounds with halogen atom (electron withdrawing groups) at C5 position showed the most potent activity. These results indicate that C5 substituted derivatives may be useful leads for anticancer drug development in the future. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Recommanded Product: 112656-95-8).

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. 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: 112656-95-8

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

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry was written by Ranasinghe, Nadeesha;Jones, Graham B.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.Category: indole-building-block This article mentions the following:

Microwave, flow and combination methodologies were applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodol. allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chem., allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Category: indole-building-block).

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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Category: indole-building-block

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, characterization, and SAR studies of new (1H-indol-3-yl)alkyl-3-(1H-indol-3-yl)propanamide derivatives as possible antimicrobial and antitubercular agents was written by Karuvalam, Ranjith Pakkath;Pakkath, Rajeesh;Haridas, Karickal Raman;Rishikesan, Rathnasamy;Kumari, Nalilu Suchetha. And the article was included in Medicinal Chemistry Research in 2013.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

In this article, we report herein the SAR studies of a series of (1H-indol-3-yl)alkyl-3-(1H-indol-3-yl)propanamides. The synthesized compounds were evaluated for their preliminary in vitro antibacterial, antifungal activity and were screened for antitubercular activity against Mycobacterium tuberculosis H37Rv strain. The synthesized compounds displayed interesting antimicrobial activity. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis 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. 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.Application In Synthesis 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

Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst was written by Egami, Hiromichi;Hotta, Ryo;Otsubo, Minami;Rouno, Taiki;Niwa, Tomoki;Yamashita, Kenji;Hamashima, Yoshitaka. And the article was included in Organic Letters in 2020.SDS of cas: 89245-41-0 This article mentions the following:

Asym. dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeded under mild reaction conditions to provide fluoropyrroloindoline derivatives I [R¹ = H, 4-Me, 5-Cl, etc.; R² = H, Me, Bn, etc.; R³ = SO₂Me, 4-MeC₆H₄SO₂, C₆H₅SO₂] in a highly enantioselective manner. Various substitution patterns on the indole ring were well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water was essential and its possible role was discussed. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0SDS of cas: 89245-41-0).

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 89245-41-0

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

Synthesis and antiviral activity of some 5′-N-phthaloyl-3′-azido-2′,3′-dideoxythymidine analogues was written by Balzarini, Jan;De Clercq, Erik;Kaminska, Beata;Orzeszko, Andrzej. And the article was included in Antiviral Chemistry & Chemotherapy in 2003.Reference of 24407-32-7 This article mentions the following:

A variety of substituted 5′-N-phthaloyl-3′-azido-2′,3′-dideoxythymidine derivatives has been evaluated for their activity against HIV-1, HIV-2 and Moloney murine sarcoma virus (MSV) in cell culture. Most of the 3′-azido-2′,3′-dideoxythymidine (AZT, zidovudine) derivatives showed antiviral activity in the lower micromolar concentration range and there was a close correlation between their anti-HIV and anti-MSV activity (r=0.99). The adamantyl phthaloyl derivative was active at submicromolar concentrations None of the compounds showed marked cytostatic activity. They did not inhibit recombinant HIV-1 reverse transcriptase. All compounds were inactive against HIV in thymidine kinase-deficient cells, pointing to the compounds’ requirement to release free AZT to afford antiviral efficacy. 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, 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.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

(NH₄)₂S₂O₈-Mediated Metal-Free Decarboxylative Formylation/Acylation of α-Oxo/Ketoacids and Its Application to the Synthesis of Indole Alkaloids was written by Dinesh, Votarikari;Nagarajan, Rajagopal. And the article was included in Journal of Organic Chemistry in 2022.COA of Formula: C9H6ClNO This article mentions the following:

A metal-free method for the formylation/acylation of indoles and β-carbolines with (NH₄)₂S₂O₈ via direct decarboxylative cross-coupling of α-oxo/ketoacids in moderate to good yields is described. The reaction occurs between ambient temperature and 40°C under mild reaction conditions with com. available starting materials. This methodol. can be expanded to some biol. active indole alkaloids like pityriacitrins, eudistomins Y₁ and Y₃, and marinacarbolines A-D. Safety: all reactions carried out in well-ventilated fume hood. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0COA of Formula: C9H6ClNO).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.COA of 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

Design and synthesis of matrine derivatives as novel anti-pulmonary fibrotic agents via repression of the TGFβ/Smad pathway was written by Li, Lingyu;Ma, Liyan;Wang, Dongchun;Jia, Hongmei;Yu, Meng;Gu, Yucheng;Shang, Hai;Zou, Zhongmei. And the article was included in Molecules in 2019.Reference of 4769-96-4 This article mentions the following:

A total of 18 matrine derivatives were designed, synthesized, and evaluated for their inhibitory effect against TGF-β1-induced total collagen accumulation in human fetal lung fibroblast MRC-5 cell lines. Among them, compound 3f displayed the most potent anti-fibrotic activity (IC50 = 3.3 ± 0.3 μM) which was 266-fold more potent than matrine. 3f significantly inhibited the fibroblast-to-myofibroblast transition and extracellular matrix production of MRC-5 cells. The TGF-β/small mothers against decapentaplegic homologs (Smad) signaling was also inhibited by 3f, as evidenced by inhibition of cytoplasm-to-nuclear translocation of Smad2/3 and suppression of TGF-β1-induced upregulation of TGF-β receptor type I (TGFβRI). Addnl., 3f exhibited potent inhibitory effects against TGF-β1-induced fibroblasts migration. These data suggested that 3f might be a potential agent for the treatment of idiopathic pulmonary fibrosis via repression of the TGFβ/Smad signaling pathway. 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. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.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