- Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations
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Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.
- Prusty, Namrata,Banjare, Shyam Kumar,Mohanty, Smruti Ranjan,Nanda, Tanmayee,Yadav, Komal,Ravikumar, Ponneri C.
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supporting information
p. 9041 - 9046
(2021/11/30)
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- Concerning the preparation of 6-bromotryptamine
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Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.
- Scott Wiens,Johnson, Jerry L.,Gribble, Gordon W.
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- 640nm excited near-infrared fluorescent dye and preparation method thereof
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The invention provides 640nm excited near-infrared fluorescent dye and a preparation method thereof. The structure of the dye is modified by nitrogen ends of a five-membered ring and a six-membered ring with different rigidities, the dye is specifically shown as a formula (1), absorption and red shift of a fluorescence spectrum are realized, and the maximum red shift is 45 nm. Meanwhile, the dye provided by the invention is high in light stability and high in quantum yield (reaching 0.3 or above in methanol), the spiral ring opening and closing forms of a bottom ring of the dye respectively correspond to colourlessness and colorless, light regulation and control can be carried out, and the dye is used for a biological fluorescent probe and super-resolution imaging of the biological fluorescent probe.
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Paragraph 0097-0101
(2020/07/13)
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- Hydrogenation or Dehydrogenation of N-Containing Heterocycles Catalyzed by a Single Manganese Complex
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A highly chemoselective base-metal catalyzed hydrogenation and acceptorless dehydrogenation of N-heterocycles is presented. A well-defined Mn complex operates at low catalyst loading (as low as 2 mol %) and under mild reaction conditions. The described catalytic system tolerates various functional groups, and the corresponding reduced heterocycles can be obtained in high yields. Experimental studies indicate a metal-ligand cooperative catalysis mechanism.
- Borghs, Jannik C.,Rueping, Magnus,Zubar, Viktoriia
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supporting information
(2020/05/19)
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- Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines
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Tandem C-N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.
- Karjee, Pallab,Sarkar, Tanumay,Kar, Subhradeep,Punniyamurthy, Tharmalingam
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p. 8261 - 8270
(2020/07/25)
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- Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid
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A Diels–Alder reaction-based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne-tethered 3-aminopyrones gives 4-substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non-canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.
- Beaudry, Christopher M.,Points, Gary L.,Stout, Kenneth T.
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supporting information
p. 16655 - 16658
(2020/12/01)
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- Indoline compounds used as immunomodulator, and preparation method thereof
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The invention relates to the technical field of medicines, and relates to indoline compounds used as an immunomodulator, stereoisomers and pharmaceutically acceptable salts thereof, a preparation method thereof, and a medicinal composition containing the
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Paragraph 0341; 0343-0345
(2019/10/01)
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- Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles
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We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.
- Huang, Honggui,Yu, Menglin,Su, Xiaolong,Guo, Peng,Zhao, Jia,Zhou, Jiabing,Li, Yi
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p. 2425 - 2437
(2018/02/23)
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- Ru(ii)-Catalyzed C7-acyloxylation of indolines with carboxylic acids
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Ruthenium(ii)-catalyzed site-selective C7-acyloxylation of indolines with carboxylic acids is presented. The substrate scope and functional group tolerance are important practical features. The kinetic isotope studies suggest that C-H bond activation may be the rate-determining step.
- De, Pinaki Bhusan,Banerjee, Sonbidya,Pradhan, Sourav,Punniyamurthy, Tharmalingam
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p. 5889 - 5898
(2018/08/21)
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- Expedient cobalt(II)-catalyzed site-selective C7-arylation of indolines with arylboronic acids
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Cobalt(ii)-catalyzed pyrimidyl directing group-assisted C7 arylation of indolines with arylboronic acids has been developed using Mn(OAc)2·4H2O as an oxidant. The use of cobalt(ii)-PCy3 as a catalyst and broad substrate scope are the important practical features.
- De, Pinaki Bhusan,Pradhan, Sourav,Banerjee, Sonbidya,Punniyamurthy, Tharmalingam
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supporting information
p. 2494 - 2497
(2018/03/21)
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- PHOSPHOINOSITIDE 3-KINASE INHIBITORS WITH ZINC BINDING MOIETY
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PROBLEM TO BE SOLVED: To provide phosphoinositide 3-kinase inhibitors with a zinc binding moiety. SOLUTION: There is provided a compound represented by formula (I) in the figure. (X is S, O or the like; Y is CH, N or the like; G1 is optionally substituted N or the like; R1 and R2 are each independently H or the like; C is a substituted heterocycle or the like; B is a linear alkyl or the like; Ra and Rb together with the nitrogen atom coupled to them are morpholino or the like; G2 is an indazole ring or the like; q, r and s are independently from 0 to 1, provided that at least one of them is 1; t is from 0 to 1; n is from 0 to 4; and p is from 0 to 2.) COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0480
(2016/10/07)
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- 1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators
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We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.
- Chekler, Eugene L. Piatnitski,Unwalla, Rayomond,Khan, Taukeer A.,Tangirala, Raghuram S.,Johnson, Mark,St. Andre, Michael,Anderson, James T.,Kenney, Thomas,Chiparri, Sue,McNally, Chris,Kilbourne, Edward,Thompson, Catherine,Nagpal, Sunil,Weber, Gregory,Schelling, Scott,Owens, Jane,Morris, Carl A.,Powell, Dennis,Verhoest, Patrick R.,Gilbert, Adam M.
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supporting information
p. 2462 - 2471
(2014/04/17)
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- Rhodium(III)-catalyzed direct regioselective synthesis of 7-substituted indoles
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An efficient, atom-economic one-pot method was developed for the preparation of 7-substituted indoles via rhodium(III)-catalyzed oxidative cross-coupling. Regioselective olefination of indoline derivatives followed by one-pot subsequent oxidation provided the desired products in good to excellent yields.
- Song, Zengqiang,Samanta, Rajarshi,Antonchick, Andrey P.
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supporting information
p. 5662 - 5665
(2013/12/04)
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- TREATMENT OF CANCERS HAVING K-RAS MUTATIONS
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The present invention provides a method of treating a cancer associated with a K-ras mutation in a subject in need thereof. The method comprises the steps of: (1) identifying a subject with a cancer associated with a K-ras mutation; and (2) administering to the subject (i) an inhibitor of PI3 kinase and (ii) an HDAC inhibitor, wherein the PI3 kinase inhibitor and the HDAC inhibitor are administered in amounts which together are therapeutically effective.
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Paragraph 0564; 0565
(2013/05/08)
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- Discovery of novel N -β- d -Xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes
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A novel series of N-linked β-d-xylosides were synthesized and evaluated for inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) in a cell-based assay. Of these, the 4-chloro-3-(4-cyclopropylbenzyl) -1-(β-d-xylopyranosyl)-1H-indole 19m was found to be the most potent inhibitor, with an EC50 value similar to that of the natural SGLT2 inhibitor phlorizin. Further studies in Sprague-Dawley (SD) rats indicated that 19m significantly increased urine glucose excretion in a dose-dependent manner with oral administration. The antihyperglycemic effect of 19m was also observed in streptozotocin (STZ) induced diabetic SD rats. These results described here are a good starting point for further investigations into N-glycoside SGLT2 inhibitors.
- Yao, Chun-Hsu,Song, Jen-Shin,Chen, Chiung-Tong,Yeh, Teng-Kuang,Hung, Ming-Shiu,Chang, Chih-Chun,Liu, Yu-Wei,Yuan, Mao-Chia,Hsieh, Chieh-Jui,Huang, Chung-Yu,Wang, Min-Hsien,Chiu, Ching-Hui,Hsieh, Tsung-Chih,Wu, Szu-Huei,Hsiao, Wen-Chi,Chu, Kuang-Feng,Tsai, Chi-Hui,Chao, Yu-Sheng,Lee, Jinq-Chyi
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experimental part
p. 166 - 178
(2011/02/28)
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- TREATMENT OF CANCERS HAVING K-RAS MUTATIONS
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The present invention provides a method of treating a cancer associated with a K- ras mutation in a subject in need thereof. The method comprises the steps of (1) identifying a subject with a cancer associated with a K-ras mutation; and (2) adminsiterign to the subject (i) an inhibitor of PI3 kinase and (ii) an HDAC inhibitor, wherein the PI3 kinase inhibitor and the HDAC inhibitor are administered in amounts which together are therapeutically effective.
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Page/Page column 224-225
(2011/11/01)
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- Quinazoline derivatives as phosphodiesterase 10 inhibitors
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The present invention if directed to certain quinazoline compounds that are PDE10 inhibitors, pharmaceutical compounds containing the same and processes for preparing the same. The invention is also directed to methods of treating diseases treatable by PD
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Page/Page column 24
(2008/06/13)
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- CINNOLINE AND QUINAZOLINE DERIVATES AS PHOSPHODIESTERASE 10 INHIBITORS
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The present invention is directed to cinnoline and quinazoline compounds of formula (I) that are PDE10 inhibitors, pharmaceutical compounds containing the same and processes for preparing the same. The invention is also directed to methods of treating diseases mediated by PDE10 enzyme such as obesity, non-insulin dependent diabetes, schizophrenia or bipolar disorder, obsessive-compulsive disorder, and the like.
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Page/Page column 81
(2010/11/28)
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- Synthesis of 6-Methoxyindoles and Indolines. Regioselective C-6 Bromination of Indolines and Subsequent Nucleophilic Substitution with a Methoxyl Group
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Regioselective bromination of the 6-position of indolines was investigated.Treatment of indolines with bromine in sulfuric acid in the presence of silver sulfate or with bromine in superacid afforded the 6-bromoindolines, which were converted to 6-methoxyindolines and indoles.
- Miyake, Yuko,Kikugawa, Yasuo
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p. 349 - 352
(2007/10/02)
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