Category: 4771-48-6

Xing, Siyang; Guo, Junsuo; Wang, Yuhan; Wang, Chenyu; Wang, Kui; Zhu, Bolin published the artcile< General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C-H activation>, Product Details of C10H9NO, the main research area is dihydropyrroloindolone preparation; isocyanate indole cycloaddition rhodium catalyst.

A [Cp*RhCl2]2-catalyzed formal [3 + 2] cycloaddition between isocyanates and indoles with electron-deficient alkenes at the C3-position of the indole moiety and directing groups at the N1-position of the indole moiety was described. Undergoing sequential coupling reaction initiated by C-H activation and aza-Michael addition, a series of 1,2-dihydropyrrolo[3,4-b]indol-3-ones I [R = Et, n-Bu, Bn, etc.; R1 = CO2Et, CO2Me, etc.; R2 = H, F, Cl, etc.; R3 = H, F, Br, etc.; R4 = H, Me, F, etc.; R5 = H, Me] was successfully afforded in moderate to good yields by the formation of one C-C bond and one C-N bond. Interestingly, the pyridyl group at the N1-position of the indole moiety not only played a role as the directing group, but also catalyzed further intramol. Michael addition as a base.

Organic Chemistry Frontiers published new progress about C-H bond activation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

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

Zhang, Ming-Zhi; Chen, Qiong; Xie, Cai-Hong; Mulholland, Nick; Turner, Sarah; Irwin, Dianne; Gu, Yu-Cheng; Yang, Guang-Fu; Clough, John published the artcile< Synthesis and antifungal activity of novel streptochlorin analogues>, Application In Synthesis of 4771-48-6, the main research area is streptochlorin analog preparation antifungal; Antifungal activity; Natural product; Streptochlorin; Structure–activity relationships; Synthesis.

Streptochlorin, first isolated as a new antibiotic in 1988 from the lipophilic extracts of the mycelium of a Streptomyces sp., is an indole natural product with a variety of biol. activities. Based on the methods developed for the synthesis of pimprinine in our laboratory, we have synthesized a series of indole-modified streptochlorin analogs and measured their activities against seven phytopathogenic fungi. Some of the analogs displayed good activity in the primary assays, and seven compounds were identified as the most promising candidates for further study. Structural optimization is still ongoing with the aim of discovering synthetic analogs with improved antifungal activity.

European Journal of Medicinal Chemistry published new progress about Fungicides. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

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

Zhang, Ming-Zhi; Mulholland, Nick; Seville, Anne; Hough, Gemma; Smith, Nicholas; Dong, Hong-Qiang; Zhang, Wei-Hua; Gu, Yu-Cheng published the artcile< First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents>, Application of C10H9NO, the main research area is pimprinine derivative analog preparation herbicidal insecticidal nematicidal.

Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biol. activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biol. assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by several compounds that possessed significant biol. activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core showed effective nematicidal activity in primary screening. Compounds 5-(benzofuran-3-yl)oxazole and 5-(benzodioxol-5-yl)oxazole were identified as the most promising lead structures for further study.

Tetrahedron published new progress about Disease, plant. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application of C10H9NO.

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

Guan, Dongliang; Rahman, Toufiqur Md; Gay, Elaine A.; Vasukuttan, Vineetha; Mathews, Kelly M.; Decker, Ann M.; Williams, Alexander H.; Zhan, Chang-Guo; Jin, Chunyang published the artcile< Indole-Containing Amidinohydrazones as Nonpeptide, Dual RXFP3/4 Agonists: Synthesis, Structure-Activity Relationship, and Molecular Modeling Studies>, Safety of 4-Methyl-1H-indole-3-carbaldehyde, the main research area is indole amidinohydrazone preparation SAR mol modeling RXFP3 RXFP4 agonist.

Herein, the first structure-activity relationship studies of a series of novel nonpeptide amidinohydrazone-based agonists I [R1 = H, 4-Me, 7-F, etc.; R2 = H, Me; R3 = ; 4-ClC6H4, 3,4-di-ClC6H3, 2-thienyl, etc.; R4 = H, Me; n = 0,1,2,3], which were characterized by RXFP3 functional and radioligand binding assays was reported. Several potent and efficacious RXFP3 agonists compound I [R1 = 5-CN-7-Me, R2 = H, R3 = 4-CO2MeC6H4, R4 = H, n = 2] were identified with EC50 values <10 nM. These compounds also had high potency at RXFP4 but no agonist activity at RXFP1, demonstrating > 100-fold selectivity for RXFP3/4 over RXFP1. In vitro ADME and pharmacokinetic assessments revealed that the amidinohydrazone derivatives might have limited brain permeability.

Journal of Medicinal Chemistry published new progress about Amidrazones Role: PAC (Pharmacological Activity), PKT (Pharmacokinetics), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Safety of 4-Methyl-1H-indole-3-carbaldehyde.

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

Wang, Zhao-Yang; Guo, Rui-Li; Zhang, Xing-Long; Wang, Meng-Yue; Chen, Gang-Ni; Wang, Yong-Qiang published the artcile< Regioselective C5-H direct iodination of indoles>, COA of Formula: C10H9NO, the main research area is iodo indole regioselective preparation; aryl iodide iodosuccinimide iodination.

An efficient regioselective C5-H direct iodination of indoles I [R = H, 6-Cl, 4-Me, etc.; R1 = C(O)H, CN, C(O)OMe, C(O)OEt] was developed for the first time. Due to the versatility of aryl iodides, the method offered a general and practical access to the C5 functionalization of indoles. The approach featured mild reaction conditions, good tolerance of functional groups and more crucially, no metal involved in the reaction, thereby benefitting the late-stage decoration of medicinal mols. A mechanistic study showed that the current iodination reaction proceeded via a radical pathway.

Organic Chemistry Frontiers published new progress about Aryl iodides Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, COA of Formula: C10H9NO.

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

Harada, Hiroshi; Hirokawa, Yoshimi; Suzuki, Kenji; Hiyama, Yoichi; Oue, Mayumi; Kawashima, Hitoshi; Yoshida, Naoyuki; Furutani, Yasuji; Kato, Shiro published the artcile< Novel and potent human and rat β3-adrenergic receptor agonists containing substituted 3-indolylalkylamines>, Name: 4-Methyl-1H-indole-3-carbaldehyde, the main research area is indolylalkylamine preparation adrenergic agonist.

A novel series of 2-(3-indolyl)alkylamino-1-(3-chlorophenyl)ethanols was prepared and evaluated for in vitro ability to stimulate cAMP production in Chinese hamster ovary cells expressing cloned human β3-adrenergic receptor (AR). The optically active I was found to be the most potent and selective human β3-AR agonist in this series with an EC50 value of 0.062 nM. In addition, the selectivity of I for human β3-AR was 210-fold and 103-fold that for human β2-AR and β1-AR, resp. Furthermore, I showed potent agonistic activity at rat β3-AR.

Bioorganic & Medicinal Chemistry Letters published new progress about Aryl aldehydes, heteroaryl Role: RCT (Reactant), RACT (Reactant or Reagent). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Name: 4-Methyl-1H-indole-3-carbaldehyde.

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

Duguta, Govardhan; Muddam, Bhooshan; Kamatala, Chinna Rajanna; Chityala, Yadaiah published the artcile< Symmetric trichloro triazine adducts with N, N'-dimethyl formamide and N, N'-dimethyl acetamide as green Vilsmeier -Haack reagents for effective formylation and acylation of Indoles>, Formula: C10H9NO, the main research area is trichloroisocyanuric acid dimethyl formamide indole formylation acetylation Vilsmeier Haack; indolecarbaldehyde acetylindole green chem.

Sym. trichloro triazine (trichlorotriazine (TCTA), and trichloroisocyanuric acid (TCCA)) adducts with N, N’-dimethyl formamide (DMF) N, N’-dimethyl acetamide (DMA) were explored as green Vilsmeier -Haack (VH) reagents for effective formylation and acetylation of indole. Reaction times (RT) reduced significantly in (TCTA/DMF), (TCCA/DMF), (TCTA/DMA) and (TCCA/DMA) triggered reactions followed by yield increments. Microwave assisted (MWA) protocols with these reagents reduced the reaction times from several hours to only few minutes followed by yield enhancements.

Chemical Data Collections published new progress about Acetylation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Formula: C10H9NO.

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

Xu, Hui; Wang, Yang-Yang published the artcile< Antifungal agents. Part 5: Synthesis and antifungal activities of aminoguanidine derivatives of N-arylsulfonyl-3-acylindoles>, Product Details of C10H9NO, the main research area is arylsulfonylacylindole aminoguanidine preparation antifungal structure activity relationship.

In order to discover more promising antifungal agents, a series of aminoguanidine derivatives of N-arylsulfonyl-3-acylindoles were prepared and evaluated in vitro for their antifungal activities against seven phytopathogenic fungi. Some of the compounds exhibited more potent antifungal activities than or comparable to hymexazol, a com. available agricultural fungicide at the concentration of 100 μg/mL. Preliminary structure-activity relationships of antifungal activities were investigated.

Bioorganic & Medicinal Chemistry Letters published new progress about Fungicides. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Product Details of C10H9NO.

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

Wang, Qinghui; Arnst, Kinsie E.; Wang, Yuxi; Kumar, Gyanendra; Ma, Dejian; Chen, Hao; Wu, Zhongzhi; Yang, Jinliang; White, Stephen W.; Miller, Duane D.; Li, Wei published the artcile< Structural Modification of the 3,4,5-Trimethoxyphenyl Moiety in the Tubulin Inhibitor VERU-111 Leads to Improved Antiproliferative Activities>, Electric Literature of 4771-48-6, the main research area is trimethoxyphenyl VERU111 synthesis tubulin antitumor.

Colchicine binding site inhibitors (CBSIs) hold great potential in developing new generations of antimitotic drugs. Unlike existing tubulin inhibitors such as paclitaxel, they are generally much less susceptible to resistance caused by the overexpression of drug efflux pumps. The 3,4,5-trimethoxyphenyl (TMP) moiety is a critical component present in many CBSIs, playing an important role in maintaining suitable mol. conformations of CBSIs and contributing to their high binding affinities to tubulin. Previously reported modifications to the TMP moiety in a variety of scaffolds of CBSIs have usually resulted in reduced antiproliferative potency. We previously reported a potent CBSI, VERU-111, that also contains the TMP moiety. Herein, we report the discovery of a VERU-111 analog I that is significantly more potent than VERU-111. The X-ray crystal structure of I in complex with tubulin confirms its direct binding to the colchicine site. In addition, I exhibited a strong inhibitory effect on tumor growth in vivo.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Electric Literature of 4771-48-6.

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

Zhang, Ming-Zhi; Chen, Qiong; Xie, Cai-Hong; Mulholland, Nick; Turner, Sarah; Irwin, Dianne; Gu, Yu-Cheng; Yang, Guang-Fu; Clough, John published the artcile< Synthesis and antifungal activity of novel streptochlorin analogues>, Computed Properties of 4771-48-6, the main research area is streptochlorin analog preparation antifungal; Antifungal activity; Natural product; Streptochlorin; Structure–activity relationships; Synthesis.

Streptochlorin, first isolated as a new antibiotic in 1988 from the lipophilic extracts of the mycelium of a Streptomyces sp., is an indole natural product with a variety of biol. activities. Based on the methods developed for the synthesis of pimprinine in our laboratory, we have synthesized a series of indole-modified streptochlorin analogs and measured their activities against seven phytopathogenic fungi. Some of the analogs displayed good activity in the primary assays, and seven compounds were identified as the most promising candidates for further study. Structural optimization is still ongoing with the aim of discovering synthetic analogs with improved antifungal activity.

European Journal of Medicinal Chemistry published new progress about Fungicides. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Computed Properties of 4771-48-6.

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