- WDR5 INHIBITORS AND MODULATORS
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Isoquinolmone compounds and derivatives inhibit WDR5 and associated protein-protein interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject, such as cancer cell proliferation.
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Paragraph 00253
(2021/05/15)
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- Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
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The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
- Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
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supporting information
p. 4302 - 4306
(2021/02/16)
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- Auto-tandem PET and EnT photocatalysis by crude chlorophyll under visible light towards the oxidative functionalization of indoles
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Chlorophyll is the most abundant photocatalytic pigment that enables plants to absorb solar energy and convert it to energy storage molecules. Herein, we report a tandem photocatalytic approach utilizing the natural pigment chlorophyll in crude form to achieve photoinduced electron transfer (PET) and energy transfer (EnT) towards the oxidative functionalization of indoles. Redox potentials, ESR, fluorescence quenching and UV experiments have evidenced the dual catalytic activity of chlorophyll. The highlight of the study is the auto-tandem photocatalytic role of chlorophyll to enable the green oxidation of indoles using molecular oxygen as the oxidant, water as the reaction medium, and photochemical energy from the visible region of the spectrum.
- Banu, Saira,Choudhari, Shubham,Patel, Girija,Yadav, Prem P.
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supporting information
p. 3039 - 3047
(2021/05/05)
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- Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks
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Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.
- Li, Liping,Gao, Hui,Sun, Ming,Zhou, Zhi,Yi, Wei
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supporting information
p. 5473 - 5478
(2020/07/14)
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- The Reaction of o-Aminoacetophenone N-Tosylhydrazone and CO2 toward 1,4-Dihydro-2H-3,1-benzoxazin-2-ones
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A transition-metal-free reaction of o-aminoacetophenone N-tosylhydrazone and CO2 has been developed, leading to a series of 1,4-dihydro-2H-3,1-benzoxazin-2-ones in moderate to good yields. This procedure proceeds with the sequential fixation of CO2 by amino leading to carbamic acid and the intra- molecular insertion of hydroxyl to carbene. (Figure presented.).
- Xiong, Hao,Wu, Xiaopeng,Wang, Hepan,Sun, Song,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 3538 - 3542
(2019/07/10)
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- Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner-Meerwein rearrangement
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A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.
- Fan, Xing,Wang, Qiang,Wei, Yin,Shi, Min
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supporting information
p. 10503 - 10506
(2018/09/21)
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- Chemoselective Alkylation of Aminoacetophenones with Alcohols by Using a Palladacycle-Phosphine Catalyst
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The development of efficient and environmentally benign palladacycle-phosphine catalyzed process to enable the formation of chemoselective C-alkylated or N-alkylated aminoacetophenones with alcohols is described. This methodology proved to be tunable by variation of the base and the temperature, which allows for the isolation of structurally diverse C-alkylated and N-alkylated aminoacetophenones. Moreover, this methodology has been applied to the synthesis of biologically and industrially important donepezil.
- Mamidala, Ramesh,Subramani, M. Siva,Samser, Shaikh,Biswal, Priyabrata,Venkatasubbaiah, Krishnan
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supporting information
p. 6286 - 6296
(2018/11/23)
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- Photo-Fries rearrangement of aryl acetamides: Regioselectivity induced by the aqueous micellar green environment
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Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be a powerful synthetic tool when it is possible to conduct it in regioselective conditions yielding a single photoproduct. Water-surfactant solutions as reaction media can be considered as an approach in this context because they show products with different features than those from isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C-N bond to yield a singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radical pair, resulting in noticeable photoproduct selectivity.
- Iguchi, Daniela,Erra-Balsells, Rosa,Bonesi, Sergio M.
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p. 105 - 116
(2016/01/20)
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- Synthesis of bridged benzazocines and benzoxocines by a titanium-catalyzed double-reductive umpolung strategy
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A sequence of two titanium(III)-catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo- and benzoxozine building blocks. The first step is a reductive cross-coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn-selectivity for the quinolone functionalization while the anti-diastereomers are obtained as the major products from chromones. With different reaction conditions, the stereochemical outcome can be altered to afford the syn-chromanone products as well. A subsequent reductive ketyl radical cyclization forges the tricyclic title compounds in good yields. A stereochemical model explaining the observed stereoselectivities is provided and the product configurations were unambiguously verified by X-ray analyses and 2D NMR spectroscopic experiments.
- Bichovski, Plamen,Haas, Thomas M.,Kratzert, Daniel,Streuff, Jan
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supporting information
p. 2339 - 2342
(2015/02/05)
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- Ru(ii)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
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Ru(ii)-catalyzed intermolecular ortho-C-H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C-N bond formation products in good yields.
- Bhanuchandra,Ramu Yadav,Rit, Raja K.,Rao Kuram, Malleswara,Sahoo, Akhila K.
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supporting information
p. 5225 - 5227
(2013/06/27)
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- QUINAZOLINE DERIVATIVES AS PDE10A ENZYME INHIBITORS
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This invention is directed to compounds, which are PDE10A enzyme inhibitors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. The pr
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Page/Page column 50; 51
(2013/04/24)
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- Selenium-promoted intramolecular oxidative amidation of 2-(arylamino)acetophenones for the synthesis of N-arylisatins
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A convenient method for the synthesis of N-arylisatins from 2-(arylamino)acetophenones by using SeO2 as an oxidant is described. Various substituted N-arylisatins were selectively obtained in good to excellent yields. The reaction tolerates a wide range of functionalities. Copyright
- Liu, Yong,Chen, Hui,Hu, Xiong,Zhou, Wang,Deng, Guo-Jun
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supporting information
p. 4229 - 4232
(2013/07/26)
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- Direct exchange of a ketone methyl or aryl group to another aryl group through ciC bond activation assisted by rhodium chelation
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Swapped: Commercially available quinolinone derivatives (1 or 2, see scheme) were reacted with arylboronic acids in the presence of a RhI complex to give aryl(quinolin-8-yl)methanone products 3 in medium to good yields. A mechanism that involves the in situ oxidation of RhI to RhIII by O2 in the presence of CuI was proposed. Copyright
- Wang, Jingjing,Chen, Weiqiang,Zuo, Sujing,Liu, Lu,Zhang, Xinrui,Wang, Jianhui
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p. 12334 - 12338
(2013/02/23)
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- Synthesis of functionalized quinolines and benzo[c][2,7]naphthyridines based on a photo-fries rearrangement
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An efficient one-pot method for the synthesis of functionalized quinolines and tetrahydronaphthyridines has been developed. The photo-Fries rearrangement of p-substituted anilides afforded differently substituted o-amino ketones that reacted in situ with acetylenic Michael acceptors such as dimethyl acetylenedicarboxylate (DMAD) to give 6,4-disubstituted quinoline 2,3-dicarboxylates. Starting from anilides derived from β-alanine, a naphthyridine nucleus can also be assembled.
- Guerrini, Giacomo,Taddei, Maurizio,Ponticelli, Fabio
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p. 7597 - 7601
(2011/11/12)
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- Setbacks and hopes: En route to the synthesis of uncialamycin
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We herein report a new approach toward the synthesis of uncialamycin, an enediyne natural product isolated from the Streptomyces uncialis, bacteria present on the surface of the lichen Cladonia uncialis. A model for the preparation of uncialamycin has bee
- Desrat, Sandy,Jean, Mickael,Van De Weghe, Pierre
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p. 7510 - 7516
(2011/10/12)
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- A general and efficient approach to 2H-indazoles and 1H-pyrazoles through copper-catalyzed intramolecular N-N bond formation under mild conditions
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A new efficient copper-catalyzed intramolecular amination reaction has been developed to readily synthesise a wide variety of multi-substituted 2H-indazole and 1H-pyrazole derivatives from easily accessible starting materials under mild conditions. A highly selective ligand for estrogen receptor β was prepared in three steps by employing this method. The Royal Society of Chemistry 2011.
- Hu, Jiantao,Cheng, Yongfeng,Yang, Yiqing,Rao, Yu
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supporting information; experimental part
p. 10133 - 10135
(2011/10/09)
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- Trifluoromethyl-promoted homocamptothecins: Synthesis and biological activity
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The homocamptothecin (hCPT) represents a new class of topoisomerase inhibitor which combines enhanced plasma stability and strong antitumor activity. Fluorine imparts desirable characteristics to drugs by modulating both the pharmacokinetics and pharmacodynamic properties of a drug. Therefore, in an attempt to improve the antitumor activity of homocamptothecins, seven new 7-trifluoromethylated homocamptothecin derivatives were prepared by proline-catalyzed Friedlander annulation. The antitumor activity in vitro and in vivo on cancer cell lines, and inhibitory properties of topoisomerase I-mediated DNA cleavage of compounds 6c and 8b were evaluated. Several of these trifluoromethylated hCPT derivatives (such as 6a, 6b and 6c) possessed higher in vitro antitumor activity than topotecan (TPT). Especially, the compound 6c showed effective in vivo antitumor activity comparable to that of TPT.
- Zhu, Lingjian,Miao, Zhenyuan,Sheng, Chunquan,Guo, Wei,Yao, Jianzhong,Liu, Wenfeng,Che, Xiaoying,Wang, Wenya,Cheng, Pengfei,Zhang, Wannian
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experimental part
p. 2726 - 2732
(2010/08/07)
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- Synthesis and bioevaluation of 22-hydroxyacuminatine analogs
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A series of 22-hydroxyacuminatine analogs was prepared by using different Friedlaender condensations. Several of the new compounds were tested for antiproliferative activity on cancer cell lines and for topoisomerase I inhibitory activity.
- Grillet, Francois,Baumlova, Barbora,Prevost, Gregoire,Constant, Jean-Francois,Chaumeron, Sophie,Bigg, Dennis C.H.,Greene, Andrew E.,Kanazawa, Alice
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p. 2143 - 2146
(2008/12/21)
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- Fries-type rearrangement of acylanilides in the presence of ytterbium triflate
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Ytterbium triflate has been used to catalyse the Fries-type rearrangement of various acylanilides with moderate yields when lithium perchlorate was used as co-catalyst.
- Su, Weike,Jin, Can
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p. 611 - 613
(2007/10/03)
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- PHENYL GUINOLINES AND THEIR USE AS ESTROGEN RECEPTOR MODULATORS
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This invention provides estrogen receptor modulators of formula: (I), having the structure wherein, R1, R2, R3, R4, R5 and R6 are as defined in the specification, or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof.
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- Non-steroidal, tetracylic compounds for estrogen-related treatments
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The invention provides non-steroidal estrogenic compounds with estrogenic and anti-estrogenic compounds effects for treatment of estrogen-deficiency related disorders, which compounds are having formula (I) wherein, one of Ra or Rb i
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- A highly practical route to 7-hydroxy-1,3-dihydro-2H-1,4-benzodiazepin- 2-one from p-anisidine
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The title compound was accessed via a Friedel-Crafts reaction on anisidine, followed by cyclization, N-methylation and O-demethylation. No column chromatography was required in the process.
- Wu, Chengde,Biediger, Ronald J.,Kogan, Timothy P.
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p. 3509 - 3516
(2007/10/03)
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- Substituent effects on the lifetimes and reactivities of arylnitrenium ions studied by laser flash photolysis and photothermal beam deflection
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Photolysis of 5-substituted-N-tert-butyl-3-methylanthranilium ion produces transient N-tert-butyl-(2-acetyl-4-substituted) phenylnitrenium ions. This is confirmed by identification of the stable products, transient absorption experiments, and photothermal
- Robbins, Rebecca J.,Laman, David M.,Falvey, Daniel E.
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p. 8127 - 8135
(2007/10/03)
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- Syntheses of Zindoxifene and Analogues by Titanium-Induced Oxo-Amide Coupling
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Highly reactive titanium on graphite is used to reductively cyclize electron-rich acylamino carbonyl compounds 7, 8, 12, 14, and 16 to the corresponding indole derivatives 9, 10, 13, 15, and 17.Compound 9b is a known precursor of the mammary tumor-inhibiting compound zindoxifene (2).The other products are new analogues of this anticancer drug, exhibiting the substitution pattern previously recognized to be essential for high pharmacological activity. - Key Words: Indoles, 2-aryl- / Titanium graphite / Zindoxifene / Tumor-growth inhibitors / Alkylidenation, intramolecular
- Fuerstner, Alois,Jumbam, Denis N.,Seidel, Guenter
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p. 1125 - 1130
(2007/10/02)
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- Synthesis and Cardiotonic Activity of a Series of Substituted 4-Alkyl-2(1H)-quinazolinones
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The synthesis, cardiac fraction III cyclic nucleotide phosphodiesterase (PDE-III) inhibition, and positive inotropic activity of a series of 2(1H)-quinazolinones are reported.A general synthesis of the series involved the cyclization of 2-aminoacetophenones with potassium cyanate in acetic acid.Modifications at the 4-position of the quinazoline nucleus were best achieved by formation of the intermediate N1-acyl-N3-phenylurea from the substituted phenyl isocyanate and appropriate carboxamide.PPA was used to ring close to the quinazoline product.Generally the SAR for the series paralleled the five-point model previously published for PDE-III inhibition.The most active analogue of the series was 5,6-dimethoxy-4-methyl-2(1H)-quinazolinone (1) (ORF 16600), which had about twice the intravenous potency of amrinone.Compound 1 is currently under development as an orally active cardiotonic.
- Bandurco, Victor T.,Schwender, Charles F.,Bell, Stanley C.,Combs, Donald W.,Kanojia, Ramesh M.,et al.
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p. 1421 - 1426
(2007/10/02)
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