3156-51-2Relevant academic research and scientific papers
Canthine analogs via intramolecular Diels-Alder reactions
Markgraf, J. Hodge,Finkelstein, Manuel,Cort, John R.
, p. 461 - 470 (1996)
Carbocyclic analogs (10 and 12) of canthine (1) and canthin-6-one (2) were prepared in three and four steps, respectively, from indole-3-carboxyaldehyde. The key step was an intramolecular Diels-Alder reaction carried out in refluxing sulfolane.
First synthesis of an indole glucosinolate
Viaud,Rollin
, p. 1417 - 1418 (1990)
The synthesis of glucobrassicin, the parent structure of the indole glucosinolate family, and its desulfoanalogue is described.
Structural elaboration of a natural product: Identification of 3,3′-diindolylmethane aminophosphonate and urea derivatives as potent anticancer agents
Kandekar, Somnath,Preet, Ranjan,Kashyap, Maneesh,Prasad M. U., Renu,Mohapatra, Purusottam,Das, Dipon,Satapathy, Shakti Ranjan,Siddharth, Sumit,Jain, Vaibhav,Choudhuri, Maitrayee,Kundu, Chanakya N.,Guchhait, Sankar K.,Bharatam, Prasad V.
, p. 1873 - 1884 (2013)
An approach involving rational structural elaboration of the biologically active natural product diindolylmethane (DIM) with the incorporation of aminophosphonate and urea moieties toward the discovery of potent anticancer agents was considered. A four-step approach for the synthesis of DIM aminophosphonate and urea derivatives was established. These novel compounds showed potent anticancer activities in two representative κidney and colon cancer cell lines, low toxicity to normal cells, higher potency than the parent natural product DIM and etoposide, and potent inhibition of cancer cell migration. Biophysical and immunological studies, including DAPI nuclear staining, western blot analysis with apoptotic protein marκers, flow cytometry, immunocytochemistry, and comet assays of the two most potent compounds revealed good efficacies in apoptosis and DNA damage. It was found that downregulation of nuclear factor κB (NF-κB p65) could be an important mode of action in apoptosis, and the two most potent derivatives were found to be more potent than parent compound DIM in the down-regulation of NF-κB. Our results show the importance of structural elaboration of DIM by rational incorporation of aminophosphonate and urea moieties to produce potent anticancer agents; they also suggest that this approach using other structurally simple bioactive natural products as scaffolds holds promise for future drug discovery and development.
Application of alkaloid streptindole and derivatives thereof in prevention and control of plant viruses and pathogenic bacteria
-
Paragraph 0016; 0030-0031, (2021/07/01)
The invention relates to an application of alkaloid streptindole and derivatives thereof in control of plant virus pathogens. It is found that streptindole and derivatives I-1 to I-14 thereof show good anti-plant virus pathogen activity for the first time
Exploiting the chiral ligands of bis(Imidazolinyl)-and bis(oxazolinyl)thiophenes—Synthesis and application in Cu-catalyzed friedel–crafts asymmetric alkylation
Al-Majid, Abdullah Mohammed,Alammari, Abdullah Saleh,Alshahrani, Saeed,Barakat, Assem,Haukka, Matti,Islam, Mohammad Shahidul
, (2021/12/17)
Five new C2-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1–L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The util-ity of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subse-quently, the optimized tridentate ligand L5 and Cu(OTf)2 catalyst (15 mol%) in toluene for 48 h promoted Friedel–Crafts asymmetric alkylation in moderate to good yields (up to 76%) and with good enantioselectivity (up to 81% ee). The bis(oxazolinyl)thiophene ligands were more potent than bis(imidazolinyl)thiophene analogues for the asymmetric induction of the Friedel–Crafts asymmetric alkylation.
Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis
Bai, Rongxian,Gao, Feng,Gu, Yanlong,Li, Minghao
supporting information, p. 7499 - 7505 (2021/10/12)
Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.
An anti-Michael route for the synthesis of indole-spiro (indene-pyrrolidine) by 1,3-cycloaddition of azomethineylide with indole-derivatised olefins
Yellappa, Shivaraj
, p. 1083 - 1089 (2019/12/30)
One-pot three-component reaction for indole-spiro (indene-pyrrolidine) highly strained molecules were synthesized with moderate yield by 1,3-cycloaddition of unsymmetrical dipolarophiles, prepared from indol-3-yl and 1-acetyl-1H-indol-3-yl derivative with azomethineylide generated through decarboxylative addition of amino acid sarcosine and ninhydrine, which is confirmed by NOESY. Our method is to demonstrate an efficient path in the preparation of strained organic spiro compound, an atom-economical process and eco-friendly toward environment. Viability gives an access to prepare of various spiro pharmaceutical drug molecules.
Amine Catalysis with Substrates Bearing N-Heterocyclic Moieties Enabled by Control over the Enamine Pyramidalization Direction
M?hler, Jasper S.,Schnitzer, Tobias,Wennemers, Helma
supporting information, p. 15623 - 15628 (2020/10/29)
Stereoselective organocatalytic C?C bond formations that tolerate N-heterocycles are valuable since these moieties are common motifs in numerous chiral bioactive compounds. Such transformations are, however, challenging since N-heterocyclic moieties can i
Streptindole and Its Derivatives as Novel Antiviral and Anti-Phytopathogenic Fungus Agents
Ding, Xin,Gao, Yongyue,Kang, Jin,Ma, Dejun,Wang, Qingmin,Wang, Ziwen,Zhang, Mingjun
, p. 7839 - 7849 (2020/09/01)
Plant diseases caused by plant viruses and pathogens seriously affect the production and storage of food crops. With the emergence of drug resistance, it is very difficult to control. Natural products are the source of new drug discovery. Here, the natural product streptindole was found to have good antiviral activity against tobacco mosaic virus (TMV) and fungicidal activities against 14 kinds of phytopathogenic fungi. A series of derivatives of streptindole were designed, synthesized, and evaluated for their antiviral and fungicidal activities. Compounds 4, 5, 11, 12c, 12d, 13d, and 13i-13l showed higher anti-TMV activities than ribavirin (inhibitory rate: 38, 37, and 40% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively), among which compound 12d (inhibitory rate: 57, 55, and 53% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity was further evaluated for the mode of action. The mechanism research revealed that 12d can break the three-dimensional structure of TMV coat protein (CP) through hydrogen bonds, thus inhibiting the assembly of virus particles. The molecular docking result showed that compound 12d did exhibit strong interaction with TMV CP. The derivatives of streptindole also displayed broad-spectrum fungicidal activities. The current study provided valuable insights into the antiviral and fungicidal activities of streptindole derivatives.
Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Indole Derivatives: Access to 1-(Trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indole and β-Carboline Derivatives
Liu, Jiaxin,Li, Longhai,Yu, Liuzhu,Tang, Lisha,Chen, Qin,Shi, Min
supporting information, p. 2959 - 2965 (2018/08/17)
A visible-light-induced trifluoromethylation of isonitrile-substituted indole derivatives has been developed from the reaction of isonitrile-substituted indoles with Togni II reagent, affording 1-(trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indoles in mo
