- Biomimetic semi-synthesis of fradcarbazole A and its analogues
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The first synthesis of fradcarbazole A (1) has been accomplished by using a biomimetic intramolecular cyclization/dehydration to construct the staurosporine-thiazole-indole skeleton. The phenyl and oxazole analogues of fradcarbazole A (2-4) were also synthesized using the same strategy. Compounds 1-4 displayed cytotoxicity against A549 cell line with IC50 values of 0.4-3.6 μM, induction of G0/G1 arrest of A549 cell cycle at 10 μM, and inhibition of PKC-β kinase with IC50 values of 0.5-0.9 μM.
- Wang, Liping,Mei, Xiangui,Wang, Cong,Zhu, Weiming
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- Reduction of 1-pyrrolyl and 1-indolyl carbamates to hemiaminals
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Hemiaminals of pyrroles and indoles have been prepared from the lithium aluminum hydride reduction of 1-pyrrolyl and 1-indolyl carbamates with good yields (67-82%). These carbamates are more reactive than aliphatic amides and carbamates under the LAH reduction, but less reactive than esters.
- Hsu, He-Chu,Hou, Duen-Ren
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- A highly chemoselective Boc protection of amines using sulfonic-acid-functionalized silica as an efficient heterogeneous recyclable catalyst
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A facile and versatile method for the chemoselective Boc protection of amines has been developed by a treatment with (Boc)2O in the presence of sulfonic-acid-functionalized silica as a catalyst. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines; aminols, amino-esters; and sulfonamides. The catalyst works under heterogeneous conditions and can be recycled.
- Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish
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- Temperature responsive phosphorescent small unilamellar vesicles
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Self-assembled lipid vesicles with embedded amphiphilic terbium(iii) complexes show a strong temperature dependence of their phosphorescence intensity and lifetime in the physiological range.
- Bhuyan, Mouchumi,Koenig, Burkhard
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- Synthesis of novel oxazolyl-indoles
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We describe the synthesis of oxazolyl-indoles that are structurally related to pimprinaphine. The effect of the indole N-cyanoalkyl substituents on the 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated oxidation was evaluated. Georg Thieme Verlag Stuttgart.
- Roy, Sudipta,Haque, Sakhina,Gribble, Gordon W.
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- Synthesis of naked amino-pyrroloindoline via direct aminocyclization of tryptamine
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The first direct access to unprotected amino-pyrroloindoline via aminocyclization of tryptamine and tryptophan has been described. A variety of structurally diverse amino-pyrroloindolines are furnished by the use of O-(2,4-dinitrophenyl)hydroxylamine (DPH
- Shen, Zhigao,Xia, Zilei,Zhao, Huijun,Hu, Jiadong,Wan, Xiaolong,Lai, Yisheng,Zhu, Chen,Xie, Weiqing
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- An efficient and highly chemoselective N-Boc protection of amines, amino acids, and peptides under heterogeneous conditions
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A simple and efficient procedure for chemoselective mono-N-Boc protection of various structurally diverse amines, amino acids, and peptides with di-tert-butyl dicarbonate using Amberlyst-15 as catalyst in ethanol is described. The catalyst can be readily separated from the reaction products with simple filtration and recovered for direct reuse. No competitive side-reactions such as formation of isocyanate, urea, oxazolidinone, and N,N-di-Boc derivatives were observed.
- Jahani, Fatemeh,Tajbakhsh, Mahmood,Khaksar, Samad,Azizi, Mohamad Reza
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- Synthesis of tetrahydro-β-carbolines, β-carbolines, and natural products, (±)-harmicine, eudistomin U and canthine by reductive Pictet Spengler cyclization
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Reductive Pictet Spengler cyclization was used for the synthesis of naturally occurring β-carbolines, eudistomin U, and canthine. Other biologically important β-carbolines as well as tetrahydro-β-carboline, such as (±)-harmicine were also synthesized usin
- Pakhare, Deepali S.,Kusurkar, Radhika S.
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- A generic approach for the catalytic reduction of nitriles
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The scope of nickel boride mediated reduction of nitriles has been extended further to allow the preparation of Boc protected amines via a mild catalytic process. It is noteworthy that the toxicity of this procedure is greatly reduced due to its catalytic
- Caddick, Stephen,Judd, Duncan B.,Lewis, Alexandra K. De K.,Reich, Melanie T.,Williams, Meredith R. V.
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- Dragmacidin e synthesis studies. Preparation of a model heptacyclic core structure
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The conversion of a cycloheptannelated indole platform into the heptacyclic core structure of dragmacidin E proceeded over nine steps. Key sequences include a cyclocondensation to form an intermediate dihydropyrazinone ring and the conversion of a cyclic urea into the cyclic guanidine of the target.
- Feldman, Ken S.,Ngernmeesri, Paiboon
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- Synthesis of novel tryptamine-based macrocycles using an Ugi 4-CR/microwave assisted click-cycloaddition reaction protocol
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A practical synthesis of novel tryptamine-based macrocycles using an Ugi 4-CR/click-cycloaddition sequential reaction protocol is described. The main features of the macrocyclic scaffolds are a peptoid moiety, a 1,3-substituted indole nucleus, and a triazole ring.
- Chavez-Acevedo, Lizbeth,Miranda, Luis D.
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- Selective Removal of N-Boc Protecting Group from Aromatic Amines Using Silica Gel-Supported Sodium Hydrogen Sulfate and HY-Zeolite as Heterogeneous Catalysts
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Silica gel-supported sodium hydrogen sulfate and HY-zeolite were found to be efficient catalysts for the selective removal of the N-Boc protecting group from aromatic amines keeping intact the aliphatic N-Boc amines. HY-zeolite was used as a reusable catalyst.
- Ravindranath,Ramesh,Reddy, M. Ravinder,Das, Biswanath
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Read Online
- Ability of the Putative Decomposition Products of 2,3-dioxetanes of Indoles to Photosensitize Cyclobutane Pyrimidine Dimer (CPD) Formation and its Implications for the “Dark” (Chemisensitized) Pathway to CPDs in Melanocytes?
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The formation of cyclobutane pyrimidine dimers (CPDs) by a “dark” pathway in melanocytes has been attributed to chemisensitization by dioxetanes produced from peroxynitrite oxidation of melanin or melanin precursors. These dioxetanes are proposed to decompose to triplet state compounds which sensitize CPD formation by triplet–triplet energy transfer. To determine whether such compounds are capable of sensitizing CPD formation, the putative decomposition products of 2,3-dioxetanes of variously substituted indoles were synthesized and their triplet state energies determined at 77?K. Their ability to photosensitize CPD formation was determined by an enzyme-coupled gel electrophoresis assay in comparison with norfloxacin (NFX) which has the lowest triplet energy known to sensitize CPD formation. The decomposition products of 2,3-dioxetanes of 5-hydroxy and 5,6-dimethoxy indoles used as models for melanin precursors had lower triplet energies and were incapable of photosensitizing CPD formation. Theoretical calculations suggest that the decomposition products of the 2,3-dioxetanes of melanin precursors DHI and DHICA will have similarly low triplet energies. Decomposition products of the 2,3-dioxetanes of indoles lacking oxygen substituents had higher triplet energies than NFX and were capable of photosensitizing CPD formation, suggesting that peroxynitrite oxidation of tryptophan could play a hitherto unrecognized role in the dark pathway to CPDs.
- Wang, Yanjing,Cacchillo, Elena M.,Niedzwiedzki, Dariusz M.,Taylor, John-Stephen
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p. 442 - 454
(2021/10/14)
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- Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole
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A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.
- Chen, Yi,Gao, Lu,Song, Xuanyi,Song, Zhenlei
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supporting information
p. 124 - 128
(2021/01/13)
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- Catalytic and Enantioselective Control of the C–N Stereogenic Axis via the Pictet–Spengler Reaction
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An unprecedented example of a chiral phosphoric acid-catalyzed atroposelective Pictet–Spengler reaction of N-arylindoles is reported. Highly enantioenriched N-aryl-tetrahydro-β-carbolines with C?N bond axial chirality are obtained via dynamic kinetic reso
- Kim, Ahreum,Kim, Aram,Park, Sunjung,Kim, Sangji,Jo, Hongil,Ok, Kang Min,Lee, Sang Kook,Song, Jayoung,Kwon, Yongseok
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supporting information
p. 12279 - 12283
(2021/05/03)
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- Access to Indole-Fused Benzannulated Medium-Sized Rings through a Gold(I)-Catalyzed Cascade Cyclization of Azido-Alkynes
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Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that α-imino gold carbene chem
- Greiner, Luca C.,Inuki, Shinsuke,Arichi, Norihito,Oishi, Shinya,Suzuki, Rikito,Iwai, Tomohiro,Sawamura, Masaya,Hashmi, A. Stephen K.,Ohno, Hiroaki
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supporting information
p. 12992 - 12997
(2021/07/20)
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- Design and synthesis of β-carboline and combretastatin derivatives as anti-neutrophilic inflammatory agents
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A series of β-carboline derivatives was synthesized by the Pictet-Spengler reaction with or without the combretastatin skeleton. The structures of these derivatives were elucidated by spectroscopic techniques. All synthesized compounds were evaluated for
- Kumar, Sunil,Wang, Yi-Hsuan,Chen, Po-Jen,Chang, Yu-Chia,Kashyap, Hemant K.,Shen, Ya-Ching,Yu, Huang-Ping,Hwang, Tsong-Long
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- KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres
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The stereoselective synthesis of 3,3′-disubstituted oxindoles having all-carbon quaternary stereocenters has been achieved using KOH as a base with an excellent diastereomeric ratio (98?:?2). The practicability of the present methodology has been validated with the synthesis of a series of substrates in good to excellent yields. The aesthetic simplicity, accessibility, and eco-friendly base (KOH) have prompted the broader application of the present methodology in organic synthesis.
- Devi, Manju,Jadhav, Amol P.,Singh, Ravi P.
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supporting information
p. 8445 - 8448
(2021/05/25)
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- N-SUBSTITUTED INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS
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The present invention provides N-substituted indoles and other heterocycles and methods of using the compounds for treating brain disorders.
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Paragraph 0231
(2020/09/12)
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- Identification of Psychoplastogenic N, N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies
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Ketamine, N,N-dimethyltryptamine (DMT), and other psychoplastogens possess enormous potential as neurotherapeutics due to their ability to potently promote neuronal growth. Here, we report the first-ever structure-Activity relationship study with the explicit goal of identifying novel psychoplastogens. We have discovered several key features of the psychoplastogenic pharmacophore and used this information to develop N,N-dimethylaminoisotryptamine (isoDMT) psychoplastogens that are easier to synthesize, have improved physicochemical properties, and possess reduced hallucinogenic potential as compared to their DMT counterparts.
- Dunlap, Lee E.,Azinfar, Arya,Ly, Calvin,Cameron, Lindsay P.,Viswanathan, Jayashri,Tombari, Robert J.,Myers-Turnbull, Douglas,Taylor, Jack C.,Grodzki, Ana Cristina,Lein, Pamela J.,Kokel, David,Olson, David E.
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p. 1142 - 1155
(2020/03/10)
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- Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates
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This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.
- Pospech, Jola,Taeufer, Tobias
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p. 7097 - 7111
(2020/06/27)
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- Aromatic heterocyclic derivative and application thereof in medicine
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The invention provides aromatic heterocyclic derivatives or stereoisomers, tautomers, nitrogen oxides, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, which are used for treating Alzheimer's disease. The invention also discloses pharmaceutical compositions containing the compounds and a method for treating Alzheimer's disease by using the compounds or the pharmaceutical compositions provided by the invention.
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Paragraph 0390; 0392-0395
(2020/02/08)
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- Tert-Butyl(3-cyano-4,6-dimethylpyridin-2-yl)carbonate as a green and chemoselective N-tert-butoxycarbonylation reagent
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The use of tert-butyl(3-cyano-4,6-dimethylpyridin-2-yl)carbonate as a chemoselective tert-butoxycarbonylation reagent for aromatic and aliphatic amines has been demonstrated. To gain insight into this reaction, in situ React IR technology was used to confirm the effectivity and chemoselectivity of this novel Boc reagent. The reaction was carried out chemoselectively in high yield under mild, environment-friendly conditions and was completed quickly within 1 hour. Simultaneously, the Boc carrier was easily recyclable, and has great application prospects for industrial production.
- Du, Fangyu,Zhou, Qifan,Fu, Yang,Zhao, Hanqi,Chen, Yuanguang,Chen, Guoliang
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supporting information
p. 6549 - 6554
(2019/05/04)
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- Selective Inhibition of Histone Deacetylase 10: Hydrogen Bonding to the Gatekeeper Residue is Implicated
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The discovery of isozyme-selective histone deacetylase (HDAC) inhibitors is critical for understanding the biological functions of individual HDACs and for validating HDACs as drug targets. The isozyme HDAC10 contributes to chemotherapy resistance and has
- Géraldy, Magalie,Morgen, Michael,Sehr, Peter,Steimbach, Raphael R.,Moi, Davide,Ridinger, Johannes,Oehme, Ina,Witt, Olaf,Malz, Mona,Nogueira, Mauro S.,Koch, Oliver,Gunkel, Nikolas,Miller, Aubry K.
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p. 4426 - 4443
(2019/05/17)
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- Fradcarbazole A compound and preparation method and application thereof
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The invention discloses a fradcarbazole A compound and a preparation method and application thereof. The fradcarbazole A compound is prepared from staurosporine or halogenated staurosporine which is subjected to a sulfur acylation reaction, a salt forming reaction together with iodomethane, a substitution reaction and a dehydrating cyclization reaction. The fradcarbazole A compound has very high selectivity and inhibitory activity on acute myeloid cell strains, namely MV4-11, with Flt3-ITD mutation, has a weak inhibiting effect on human peripheral blood mononuclear cells (PBMC), and can be developed to be an efficient and low-toxicity drug for preventing and treating leukemia.
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Paragraph 0017
(2019/07/01)
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- A Desymmetrization-Based Total Synthesis of Reserpine
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Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.
- Park, Jisook,Chen, David Y.-K.
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supporting information
p. 16152 - 16156
(2018/11/23)
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- A catalytic N-deacylative alkylation approach to hexahydropyrrolo[2,3-b]indole alkaloids
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A versatile unprecedented strategy to diversely functionalized hexahydropyrrolo[2,3-b]indole alkaloids is described in high chemical yields. The synthesis features a key Pd(0)-catalyzed deacylative alkylation of N-acyl 3-substituted indoles using only 1 mol% of Pd(PPh3)4. The scope of this methodology is further defined in the asymmetric synthesis of pyrroloindolines using a diastereoselective approach.
- Kumar, Nivesh,Maity, Arindam,Gavit, Vipin R.,Bisai, Alakesh
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supporting information
p. 9083 - 9086
(2018/08/21)
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- Relay Catalysis of Rh (II) and Cobaloxime: Stereoselective Synthesis of Spiroindanones from N-Sulfonyl-1,2,3-triazoles
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A novel relay Rh (II)/cobaloxime (III) dual catalysis strategy has been developed for the stereoselective synthesis of indolyl spiroindanones from readily accessible N-sulfonyl-1,2,3-triazoles. This binary-catalyst system enables an aza-vinyl carbene init
- Liu, Zhao,Du, Qiuchen,Zhai, Hongbin,Li, Yun
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supporting information
p. 7514 - 7517
(2018/12/11)
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- INDOLE AHR INHIBITORS AND USES THEREOF
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The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.
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Paragraph 00308-00309
(2018/11/22)
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- Des-Formylflustrabromine (dFBr): A Structure-Activity Study on its Ability to Potentiate the Action of Acetylcholine at α4β2 Nicotinic Acetylcholine Receptors
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The naturally-occurring indole alkaloid des-formylflustrabromine (dFBr; 1) is one of the first agents shown to act as a selective positive allosteric modulator (PAM) at α4β2 nicotinic acetylcholine receptors (nAChRs). We previously deconstructed this agent to determine which of its structural features contribute to its actions and formulated a "working pharmacophore". Here, we elaborate the dFBr (1; EC50 = 0.6 μM) structure to identify how various structural modifications impact its actions. Electrophysiological studies with Xenopus laevis oocytes identified several compounds with dFBr-like potency and one, the 5-bromo analog of 1 (i.e., 5-bromo dFBr; 25; EC50 = 1.6 μM), with more than twice the efficacy of 1 as a PAM at α4β2 nAChRs.
- Dukat, Malgorzata,Jain, Atul D.,German, Nadezhda,Ferrara-Pontoriero, Rossana,Huang, Yanzhou,Ma, Yilong,Schulte, Marvin K.,Glennon, Richard A.
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- Direct C?H Phosphonylation of Electron-Rich Arenes and Heteroarenes by Visible-Light Photoredox Catalysis
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The direct transformation of ubiquitous, but chemically inert C?H bonds into diverse functional groups is an important strategy in organic synthesis that improves the atom economy and faclitates the preparation and modification of complex molecules. In contrast to the wide applications of aryl phosphonates, their synthesis via direct C?H bond phosphonylation is a less explored area. We report here a general, mild, and broadly applicable visible-light photoredox C?H bond phosphonylation method for electron-rich arenes and heteroarenes. The photoredox catalytic protocol utilizes electron-rich arenes and biologically important heteroarenes as substrates, [Ru(bpz)3][PF6]2 as photocatalyst, ammonium persulfate as oxidant, and trialkyl phosphites as the phosphorus source to provide a wide range of aryl phosphonates at ambient temperature under very mild reaction conditions.
- Shaikh, Rizwan S.,Ghosh, Indrajit,K?nig, Burkhard
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supporting information
p. 12120 - 12124
(2017/09/13)
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- COMPOUNDS AND METHODS FOR THE SYNTHESIS OF 5-(N-PROTECTED-TRYPTAMINOCARBOXYAMIDE)-2'-DEOXYURIDINE PHOSPHORAMIDATE FOR INCORPORATION INTO A NUCLEIC SEQUENCE
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Modified Tryptamine, Tryptamine-2'-deoxy-uridine (TrpdU) and TrpdU-phosphoramidites for oligonucleotide synthesis are provided, as well as improved methods of their synthesis and oligonucleotides comprising at least one modified TrpdU nucleotide.
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Paragraph 0034; 0078-0081
(2017/10/11)
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- An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives
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An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.
- Xu, Jun,Tong, Rongbiao
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supporting information
p. 2952 - 2956
(2017/07/24)
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- Palladium-catalysed direct C-2 methylation of indoles
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A direct C-2 methylation reaction of indoles bearing a readily removable N-2-pyrimidyl moiety as a site-specific directing group has been developed with a palladium catalyst. This reaction relied on the use of KF to promote efficient methylation. A moderate to good yield was achieved in a range of indole substrates.
- Tu, Daoquan,Cheng, Xiuzhi,Gao, Yadong,Yang, Panpan,Ding, Yousong,Jiang, Chao
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supporting information
p. 7443 - 7446
(2016/08/16)
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- Bisindolyl maleimide derivative and preparation method and application thereof
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The invention provides a bisindolyl maleimide derivative and a preparation method and application thereof. The bisindolyl maleimide derivative has an excellent alpha-glucosidase inhibition effect and can be used for preventing and treating diabetes.
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Paragraph 0713
(2017/01/02)
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- Method for preparing spiro2-diazido-indoline
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The invention provides a method for preparing a compound shown in the formula II (please see the formula in the description). The method includes the following step of making indole shown in the formula I (please see the formula in the description) react with a precursor and ceric ammonium nitrate in the inert atmosphere so that spiro2-diazido-indoline can be obtained, wherein the precursor can provide azide groups. In the formula I and the formula II, R1 is selected from at least one of hydrogen, an alkyl group of C1-C5, alkoxy of C1-C5, F, Br and Cl; R2 is an alkyl group of C1-C5; Boc represents t-butyloxycarboryl. The precursor is sodium azide or trimethylsilyl azide. The mole ratio of indole shown in the formula I to the precursor to ceric ammonium nitrate is 1:(2-4):(4-8). According to the simple method, the two azide groups are introduced to the organic molecule, and in other words, spiro2-diazido-indoline is effectively prepared under the effects of the precursor capable of providing the azide groups and ceric ammonium nitrate with indole of different structures as the raw material. The raw material is easy to prepare, the reaction condition is gentle, operation is easy and convenient, and yield can reach 45% at most.
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Paragraph 0038; 0039
(2016/10/09)
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- Bisindolylmaleimide derivative, and preparation method and use thereof
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The invention provides a bisindolylmaleimide derivative, and a preparation method and a use thereof. The bisindolylmaleimide derivative has a good tumor treatment effect, especially has a good treatment effect on some drug-resistant tumors, and can realize accurate treatment of the drug-resistant tumors.
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Paragraph 0715; 0716
(2017/04/03)
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- Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles
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A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.
- Holzapfel, Cedric,Dasilva, Etelinda,Den Drijver, Laetitia,Bredenkamp, Tyler
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p. 2912 - 2915
(2016/09/28)
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- SUBSTITUTED DIAMINOPYRIMIDYL COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
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Provided herein are diaminopyrimidyl Compounds having the following structures: wherein X, L, R1, and R2 are as defined herein, compositions comprising an effective amount of a Diaminopyrimidyl Compound, and methods for treating or preventing PKC-theta-mediated disorders, or a condition treatable or preventable by inhibition of a kinase, for example, PKC-theta.
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Paragraph 0467
(2015/07/02)
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- CuCl2/TBHP-mediated direct chlorooxidation of indoles
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CuCl2/TBHP-mediated direct chlorooxidation of indole derivatives under simple aerobic conditions was reported, leading to facile preparations of a range of 3,3-disubstituted 3-chlorooxindoles in good yields and selectivities.
- Wang, Huifei,Liu, Dong,Chen, Huiyu,Li, Jing,Wang, David Zhigang
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supporting information
p. 7073 - 7076
(2015/08/19)
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- Access to Spirocyclized Oxindoles and Indolenines via Palladium-Catalyzed Cascade Reactions of Propargyl Carbonates with 2-Oxotryptamines and Tryptamines
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(Chemical Equation Presented). Reported here are methods for the direct construction of a range of spirocyclized oxindoles and indolenines in good to excellent yields. Specifically, we report the palladium-catalyzed reactions of oxindoles and indoles, both functioning as bis-nucleophiles, with propargyl carbonates to afford spirocyclic products having an exocyclic double bond on the newly formed ring. The reaction proceeds through a process wherein the first nucleophilic unit on the oxindole or indole reacts with an allenyl-palladium species, formed from oxidative addition of Pd(0) to propargyl carbonates, to generate a π-allyl palladium intermediate that then reacts further with the second nucleophilic component of the oxindole or indole. The cascade process forges two bonds en route to spirocyclized oxindole and indolenine products. The use of chiral phosphines renders the cyclization sequence enantioselective, providing spirocyclic products with modest to good enantioselectivities.
- Nibbs, Antoinette E.,Montgomery, Thomas D.,Zhu, Ye,Rawal, Viresh H.
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p. 4928 - 4941
(2015/06/02)
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- Zinc chloride promoted efficient and facile BOC protection of amines
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Amines are efficiently protected as their BOC derivatives under mild reaction conditions when reacted with BOC anhydride in presence of ZnCl2. The present method is applicable to a variety of amines including aliphatic, aromatic as well as heteroaromatic amines. This protocol appears to be competitive and in some cases superior to previously reported procedures that work under basic conditions.
- Arifuddin, M.,Lakshmikant, N.,Rajasekar, N.,Shinde, D. B.
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p. 1168 - 1172,5
(2020/08/31)
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- INHIBITION OF BACTERIAL BIOFILMS WITH ARYL CARBAMATES
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Disclosure is provided for carbamate compounds that prevent, remove and/or inhibit the formation of biofilms, compositions including these compounds, devices including these compounds, and methods of using the same.
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Page/Page column 33-34
(2012/02/01)
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- Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups
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A simple and efficient method for the chemoselective N-Boc protection of the amine moiety in a variety of compounds is described using di-tert-butyl dicarbonate and guanidine hydrochloride as an organocatalyst in ethanol at 35-40°C. Selective mono-N-Boc protection of diamines and chemoselective protection of hydroxylamines without formation of any side products is achieved. Amino acids and peptides are N-Boc protected efficiently in excellent yields under convenient reaction conditions.
- Jahani, Fatemeh,Tajbakhsh, Mahmood,Golchoubian, Hamid,Khaksar, Samad
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supporting information; experimental part
p. 1260 - 1264
(2011/04/15)
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- The enantioselective, organocatalyzed Diels-Alder reaction of 2-Vinlindoles with α,β-unsaturated aldehydes: An efficient route to functionalized tetrahydrocarbazoles
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(Figure Presented) Prolinol catalysts: A highly enantioand diastereoselective prolinol-catalyzed Diels-Alder reaction of 2-vinylindoles and α,β-unsaturated aldehydes is developed (see scheme). This methodology allows the development of further applications of prolinols in asymmetric synthesis. The resulting densely functionalized enantiomerically pure tetrahydrocarbazoles are useful in the total synthesis of natural products such as the core structure of the akuammiline alkaloid vincorine.
- Zheng, Changwu,Lu, Yingpeng,Zhang, Junkang,Chen, Xingkuan,Chai, Zhuo,Ma, Wenying,Zhao, Gang
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supporting information; experimental part
p. 5853 - 5857
(2010/09/04)
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- New synthetic technologies for the construction of heterocycles and tryptamines
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New synthetic methods for the construction of novel heterocycles and tryptamines are described. Thus, N-Boc anilines (I) are sequentially converted to heterocycles II ((3-(2-aminophenyl)pyrrolidin-3-ol) derivatives),III (substituted 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrol idines), and VI (2-(4,5-dihydro-1H-pyrrol-3-yl)aniline) derivatives through a route involving t-BuLi induced ortho-metalation/ LaCl3 2LiCl metalexchange, reaction with N-Boc pyrrolidin-3-one (5), and subsequent deca rboxylative fragmentation. Labile intermediates VI are effectively converted to tryptamines Xa and Xb under controlled proticacidconditions.Inadditiontoprovidingexpedientaccesstothe2-oxo- 1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrolidines (III), the method is applicable to the synthesis of the corresponding 2-oxo-1,2-dihydrospirobenzo[d] [1,3]oxazine-4,3'-piperidine series of spirocycles (e.g., 42) and their precursors (3-(2-aminophenyl)piperidin-3-ol derivatives, e.g., 43) by using N-Boc-protected piperidin-3-one (40). Applications of the developed synthetic technologies to the synthesis of regioisomeric spirocycles 87 and 90, tryptamines 88 and 91, Corey's aspidophytine tryptamine (97), and efavirenz (1) are also described.
- Nicolaou, K. C.,Krasovskiy, Arkady,Majumder, Utpal,Trepanier, Vincent E.,Chen, David Y.-K.
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supporting information; experimental part
p. 3690 - 3699
(2009/09/24)
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- Boiling water-catalyzed neutral and selective N-Boc deprotection
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A general protocol for removing Boc groups from various types of nitrogen is reported and a preliminary investigation of the reaction mechanism indicates that water acts as a dual acid/base catalyst at elevated temperature. The Royal Society of Chemistry 2009.
- Wang, Jia,Liang, Yan-Liang,Qu, Jin
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supporting information; experimental part
p. 5144 - 5146
(2009/12/08)
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- An expedient strategy for the synthesis of tryptamines and other heterocycles
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(Chemical Equation Presented) Making many from one: N-Boc-protected anilines are converted into an array of useful N-heterocycles and tryptamines through an expedient, cascade-based synthetic sequence involving ortho metalation and subsequent coupling wit
- Nicolaou,Krasovskiy, Arkady,Trepanier, Vincent E.,Chen, David Y.-K.
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supporting information; experimental part
p. 4217 - 4220
(2009/03/12)
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- Discovery of N1-(6-Chloroimidazo[2,1-b][1,3]-thiazole-5- sulfonyl)tryptamine as a potent, selective, and orally active 5-HT6 receptor agonist
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N1-Arylsulfonyltryptamines have been identified as 5-HT 6 receptor ligands. In particular, N1(6-chloroimidazo[2,1- b][1,3]thiazole-5-sulfonyl)tryptamine (11q) is a high affinity, potent full agonist (5-HT6 Ksub
- Cole, Derek C.,Stock, Joseph R.,Lennox, William J.,Bernotas, Ronald C.,Ellingboe, John W.,Boikess, Steve,Coupet, Joseph,Smith, Deborah L.,Leung, Louis,Zhang, Guo-Ming,Feng, Xidong,Kelly, Michael F.,Galante, Rocco,Huang, Pingzhong,Dawson, Lee A.,Marquis, Karen,Rosenzweig-Lipson, Sharon,Beyer, Chad E.,Schechter, Lee E.
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p. 5535 - 5538
(2008/03/15)
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- Simple and selective removal of the t-butyloxycarbonyl (Boc) protecting group on indoles, pyrroles, indazoles, and carbolines
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A highly selective and efficient deprotection of the N-t-butoxy carbonyl (N-Boc) group on indoles, pyrroles, indazoles, and carbolines has been achieved in high yields using a catalytic amount of NaOMe as a base in dry MeOH, at ambient temperature. Copyright Taylor & Francis Group, LLC.
- Ravinder,Reddy, A. Vijender,Mahesh, K. Chinni,Narasimhulu,Venkateswarlu
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p. 281 - 287
(2007/10/03)
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- Catalytic asymmetric hydrogenation of indoles using a rhodium complex with a chiral bisphosphine ligand PhTRAP
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Highly enantioselective hydrogenation of N-protected indoles was successfully developed by use of the rhodium catalyst generated in situ from [Rh(nbd)2]SbF6 and the chiral bisphosphine PhTRAP, which can form a trans-chelate complex with a transition metal atom. The PhTRAP-rhodium catalyst required a base (e.g., Cs2CO3) for the achievement of high enantioselectivity. Various 2-substituted N-acetylindoles were converted into the corresponding chiral indolines with up to 95% ee. The hydrogenations of 3-substituted N-tosylindoles yielded indolines possessing a stereogenic center at the 3-position with high enantiomeric excesses (up to 98% ee).
- Kuwano, Ryoichi,Kashiwabara, Manabu,Sato, Koji,Ito, Takashi,Kaneda, Kohei,Ito, Yoshihiko
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p. 521 - 535
(2007/10/03)
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- Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation
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(Chemical Equation Presented) A new and efficient synthetic route to chiral 3-substituted hexahydropyrroloindoline 18 possessing absolute configurations in accordance with indole alkaloids has been developed from readily available L-tryptophan. The key step relies on the one-pot cascade reaction of oxazolidinone 17 with diazoester, which proceeds through intermolecular cyclopropanation, ring opening, and cyclization.
- Song, Hao,Yang, Jun,Chen, Wei,Qin, Yong
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p. 6011 - 6014
(2007/10/03)
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