cas 4456-77-3, 1,2,3,4-Tetrahydroisoquinoline-1,3-dione

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FUSED-GLUTARIMIDE CRBN LIGANDS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same. The present invention also relates to compounds and methods useful for binding and modulating the activity of cereblon (CRBN), especially for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.
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(2021/02/12)

4-benzylideneisoquinoline-1,3(2H,4H)-diones as tyrosyl DNA phosphodiesterase 2 (TDP2) inhibitors
Tyrosyl-DNA phosphodiesterase 2 (TDP2) repairs topoisomerase II (Top2) mediated DNA damages, including double-strand breaks (DSBs) that underpin the anticancer mechanism of clinical Top2 poisons such as etoposide (ETP). Inhibition of TDP2 could sensitize
Senaweera, Sameera,He, Tianyu,Cui, Haixi,Aihara, Hideki,Wang, Zhengqiang
p. 371 - 386
(2020/11/23)

Enantioselective synthesis of isoquinoline-1,3(2: H,4 H)-dione derivatives via a chiral phosphoric acid catalyzed aza-Friedel-Crafts reaction
A highly enantioselective aza-Friedel-Crafts reaction of structurally new ketimines with indoles and pyrrole is developed by using a chiral phosphoric acid as the catalyst. This protocol enables the first enantioselective synthesis of isoquinoline-1,3(2H,
You, Yong,Lu, Wen-Ya,Xie, Ke-Xin,Zhao, Jian-Qiang,Wang, Zhen-Hua,Yuan, Wei-Cheng
supporting information
p. 8478 - 8481
(2019/07/22)

A Cu-Doped ZIF-8 metal organic framework as a heterogeneous solid catalyst for aerobic oxidation of benzylic hydrocarbons
Mixed-metal metal organic frameworks have received considerable attention in recent years and it has been shown that the activity of the parent metal organic framework (MOF) is often enhanced upon doping with external metal ions within the framework. In this context, Cu2+ ions with different loadings were incorporated within the ZIF-8 framework to obtain a series of Cu-doped ZIF-8 materials and their activity was examined in the aerobic oxidation of hydrocarbons. The as-synthesized Cu-doped solids were characterized by powder X-ray diffraction (XRD), ultraviolet diffuse reflectance spectroscopy (UV-DRS), scanning electron microscopy (SEM), Fourier Transform infrared (FT-IR), electron paramagnetic resonance (EPR) and inductively coupled plasma (ICP) analysis. The experimental results revealed that the activity of Cu-doped ZIF-8 is much higher than that of the parent ZIF-8 in all the tested substrates at 120 °C. Furthermore, the activity of the Cu-doped ZIF-8 with the highest Cu loading was eight fold higher than that of the parent ZIF-8 in the aerobic oxidation of cyclooctane (1) at 120 °C with more than 80% selectivity to the corresponding cyclooctanol/cyclooctanone (ol/one) mixture. Cu-doped ZIF-8 was reused two times with no significant drop in its activity under identical conditions. Furthermore, comparison of the two times reused solid with that of the fresh solid by powder XRD and SEM analysis revealed identical structural integrity and morphology, respectively during the oxidation reactions.
Nagarjun, Nagarathinam,Dhakshinamoorthy, Amarajothi
p. 18702 - 18712
(2019/12/09)

Superelectrophiles in Synthesis: Preparation of Aromatic Imides
Aromatic carboxylic acids are found to undergo reactions with isocyanates, wherein triflic acid promotes the formation of aromatic imide products in fair to good yields. It is proposed that the carboxylic acid group directs the isocyanate electrophile to
Kennedy, Sean H.,Schaeff, Mark N.,Klumpp, Douglas A.
p. 14133 - 14140
(2019/10/16)

Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids
A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)-cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.
Hu, Kun,Qi, Linjun,Yu, Shuling,Cheng, Tianxing,Wang, Xiaodong,Li, Zhaojun,Xia, Yuanzhi,Chen, Jiuxi,Wu, Huayue
p. 1740 - 1750
(2017/06/07)

2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions
The synthesis of biologically relevant homophthalimide and 3-aminoisocoumarin nuclei via palladium-catalyzed carbonylation of 2-(2-iodoaryl)acetamides has been developed. The degree of N-substitution on the starting amide substrate dictates whether C?N or
Frutos-Pedre?o, Roberto,García-López, José-Antonio
supporting information
p. 2692 - 2700
(2016/08/30)

Exploration of the nicotinamide-binding site of the tankyrases, identifying 3-arylisoquinolin-1-ones as potent and selective inhibitors in vitro
Tankyrases-1 and -2 (TNKS-1 and TNKS-2) have three cellular roles which make them important targets in cancer. Using NAD+ as a substrate, they poly(ADP-ribosyl)ate TRF1 (regulating lengths of telomeres), NuMA (facilitating mitosis) and axin (in wnt/β-catenin signalling). Using molecular modelling and the structure of the weak inhibitor 5-aminoiso quinolin-1-one, 3-aryl-5-substituted-isoquinolin-1-ones were designed as inhibitors to explore the structure-activity relationships (SARs) for binding and to define the shape of a hydrophobic cavity in the active site. 5-Amino-3-arylisoquinolinones were synthesised by Suzuki-Miyaura coupling of arylboronic acids to 3-bromo-1-methoxy-5-nitro-isoquinoline, reduction and O-demethylation. 3-Aryl-5-methylisoquinolin-1-ones, 3-aryl-5-fluoroisoquinolin-1-ones and 3-aryl-5-methoxyisoquinolin-1-ones were accessed by deprotonation of 3-substituted-N,N,2-trimethylbenzamides and quench with an appropriate benzonitrile. SAR around the isoquinolinone core showed that aryl was required at the 3-position, optimally with a para-substituent. Small meta-substituents were tolerated but groups in the ortho-positions reduced or abolished activity. This was not due to lack of coplanarity of the rings, as shown by the potency of 4,5-dimethyl-3-phenylisoquinolin-1-one. Methyl and methoxy were optimal at the 5-position. SAR was rationalised by modelling and by crystal structures of examples with TNKS-2. The 3-aryl unit was located in a large hydrophobic cavity and the para-substituents projected into a tunnel leading to the exterior. Potency against TNKS-1 paralleled potency against TNKS-2. Most inhibitors were highly selective for TNKSs over PARP-1 and PARP-2. A range of highly potent and selective inhibitors is now available for cellular studies.
Paine, Helen A.,Nathubhai, Amit,Woon, Esther C.Y.,Sunderland, Peter T.,Wood, Pauline J.,Mahon, Mary F.,Lloyd, Matthew D.,Thompson, Andrew S.,Haikarainen, Teemu,Narwal, Mohit,Lehti?, Lari,Threadgill, Michael D.
supporting information
p. 5891 - 5908
(2015/11/11)

DENGUE AND WEST NILE VIRUS PROTEASE INHIBITORS
Compounds and methods of treating or preventing a Flavivirus infection in a subject are provided. The methods comprise administering to the subject a therapeutically effective amount of a compound as described herein. The methods are useful in treating and/or preventing Flavivirus infections such as, for example, West Nile Virus, Dengue Virus, and Japanese Encephalitis Virus. Methods of inhibiting a Flavivirus protease in a cell are also provided.
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Page/Page column 36

(2014/10/18)

PYRIDINE AND ISOQUINOLINE DERIVATIVES AS SYK- AND JAK-KINASE INHIBITORS
The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by inhibition of Syk kinase and/or Janus kinases.
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Page/Page column 56-57

(2012/04/17)

Pyridine- and isoquinoline-derivatives as Syk and JAK kinase inhibitors
The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by inhibition of Syk kinase and/or Janus kinases.
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Paragraph 0172

(2013/03/26)

A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles
The one-pot, three-component reaction of substituted homophthalic anhydrides with hydrazine in DMF as solvent and reactant, at reflux temperature, afforded isochromeno[3,4-c]pyrazole-5(2H)-one derivatives in high yields. The mechanism and roles of the substrates were investigated and it was found that cyclic hydrazides were formed as intermediates.
Ozcan, Sevil,Dengiz, Cagatay,Deli?meroglu, Murat K.,Sahin, Ertan,Balci, Metin
scheme or table
p. 1495 - 1497
(2011/05/16)

Synthesis and reactivity of ortho-palladated phenylacetamides. Intramolecular C-N vs C-O reductive coupling after CO or XyNC insertion into the Pd-C bond. Synthesis of isoquinoline- and isocoumarin-based heterocycles
Aryl palladium complexes [Pd{C6H4CH 2C(O)NRR′-2}I(N^N)] (N^N = N,N,N′,N′- tetramethylethylenediamine = tmeda, NRR′ = NH2 (1a), NHMe (1b), NMe2 (1c); N^N = 4,4′-di-tert-butyl-2,2′-bipyridyl (dbbpy), NR
Vicente, Jose,Gonzalez-Herrero, Pablo,Frutos-Pedreno, Roberto,Chicote, Maria-Teresa,Jones, Peter G.,Bautista, Delia
experimental part
p. 1079 - 1093
(2011/04/25)

SUBSTITUTED AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
The invention relates to substituted aromatic carboxamide and urea derivatives, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions (formula (I)).
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Page/Page column 136; 137

(2010/11/18)

4-(Phenylaminomethylene)isoquinoline-1,3(2H,4H)-diones as potent and selective inhibitors of the cyclin-dependent kinase 4 (CDK4)
The cyclin-dependent kinases (CDKs), as complexes with their respective partners, the cyclins, are critical regulators of cell cycle progression. Because aberrant regulations of CDK4/cyclin D1 lead to uncontrolled cell proliferation, a hallmark of cancer, small-molecule inhibitors of CDK4/cyclin D1 are attractive as prospective antitumor agents. The series of 4-(phenylaminomethylene)isoquinoline-1,3(2H,4H)-dione derivatives reported here represents a novel class of potent inhibitors that selectively inhibit CDK4 over CDK2 and CDK1 activities. In the headpiece of the 4-(phenylaminomethylene) isoquinoline-1,3(2H,4H)-dione, a basic amine substitutent is required on the aniline ring for the CDK4 inhibitory activity. The inhibitory activity is further enhanced when an aryl or heteroaryl substituent is introduced at the C-6 position of the isoquinoline-1,3(2H,4H)-dione core. We present here SAR data and a CDK4 mimic model that explains the binding, potency, and selectivity of our CDK4 selective inhibitors.
Tsou, Hwei-Ru,Otteng, Mercy,Tran, Tritin,Floyd Jr., M. Brawner,Reich, Marvin,Birnberg, Gary,Kutterer, Kristina,Ayral-Kaloustian, Semiramis,Ravi, Malini,Nilakantan, Ramaswamy,Grillo, Mary,McGinnis, John P.,Rabindran, Sridhar K.
scheme or table
p. 3507 - 3525
(2009/04/07)

In vitro structure-activity relationship and in vivo characterization of 1-(aryl)-3-(4-(amino)benzyl)urea transient receptor potential vanilloid 1 antagonists
The synthesis and structure-activity relationship of 1-(aryl)-3-(4-(amino) benzyl)urea transient receptor potential vanilloid 1 (TRPV1) antagonists are described. A variety of cyclic amine substituents are well tolerated at the 4-position of the benzyl group on compounds containing either an isoquinoline or indazole heterocyclic core. These compounds are potent antagonists of capsaicin activation of the TRPV1 receptor in vitro. Analogues, such as compound 45, have been identified that have good in vivo activity in animal models of pain. Further optimization of 45 resulted in compound 58 with substantially improved microsome stability and oral bioavailability, as well as in vivo activity.
Perner, Richard J.,DiDomenico, Stanley,Koenig, John R.,Gomtsyan, Arthur,Bayburt, Erol K.,Schmidt, Robert G.,Drizin, Irene,Guo, Zhu Zheng,Turner, Sean C.,Jinkerson, Tammie,Brown, Brian S.,Keddy, Ryan G.,Lukin, Kurill,McDonald, Heath A.,Honore, Prisca,Mikusa, Joe,Marsh, Kennan C.,Wetter, Jill M.,St. George, Karen,Jarvis, Michael F.,Faltynek, Connie R.,Lee, Chih-Hung
p. 3651 - 3660
(2008/02/12)

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity, wherein X1, X2, X3, X4, X5, R5, R6, R7, R8a, R8b, R9, Z1, Z2 and L are as defined in the description.
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(2008/06/13)

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.
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Page/Page column 29-30

(2010/02/11)

Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
Compounds of formula (I) are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.
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(2008/06/13)

Silica supported MoO3: A mild heterogeneous catalyst for the Beckmann rearrangement and its application to some sugar derived ketoximes
Silica supported molybdenum(VI) oxide (20%) has been explored as a new solid catalyst for the Beckmann rearrangement and the results are compared in parallel with the known β-zeolite as a catalyst for the same transformation. Both catalysts were found to facilitate the rearrangement under mild conditions and the conditions employed were tolerable for protecting groups such as isopropylidene, cyclohexylidene and PMB are commonly employed in carbohydrate chemistry.
Dongare, Mohan K.,Bhagwat, Vivekanand V.,Ramana,Gurjar, Mukund K.
p. 4759 - 4762
(2007/10/03)

Isoquinolinone derivatives
Derivatives of isoquinolinone and dihydrolisoquinolinone, and related compounds, and their use as pharmaceuticals in the treatment of a disease by inhibition of the enzyme poly(ADP-ribose)polymerase (“PARP”) are disclosed.
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(2008/06/13)

Fused pyridine derivatives
The present provides a condensed pyridine compound (I) represented by the following formula: (wherein, R2represents ring A represents benzene ring, pyridine ring, thiophene ring or furan ring; and B represents its pharmaceutically acceptable salt or hydrates thereof, which is a clinically useful medicament having a serotonin antagonism, in particular, that for treating, ameliorating or preventing spastic paralysis or central muscle relaxants for ameliorating myotonia.
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Example 17

(2010/01/30)

An efficient method for one-carbon elongation of aryl aldehydes via their dibromoalkene derivatives
Various aryl aldehydes were efficiently converted into one-carbon extended aryl acetamides or aryl acetic acids through the reaction of their dibromoalkene derivatives with pyrrolidine in the presence of water under very mild conditions.
Huh, Dal Ho,Jeong, Ji Sang,Lee, Hee Bong,Ryu, Hoejin,Kim, Young Gyu
p. 9925 - 9932
(2007/10/03)

On the reactions of 1,3-isoquinolinediones with singlet oxygen
Reactions of 1,3-isoquinolinediones 5 and 4-alkylated 1,3- isoquinolinediones 13 with singlet oxygen are entirely dominated by their enolization and proceed smoothly in benzene in the presence of pyridine as a base and a hydrogen bond acceptor. The products are triketones 6 and benzoisofuranones 7 for 5, and hydroperoxides 14, hydroxides 15 and benzoisofuranones 16 for 13. It was found that hydrolysis of 6 afforded the isoindolones 8 and not products 7, whereas alkaline cleavage of the hydroperoxide 14a yielded not only 16a, but also the isoindolone 19a, In view of these observations, an unusual [4+2] cycloaddition of the electron-rich enol 21 with singlet oxygen is proposed to be responsible for the formation of products 7 and 16, while products 6, 14 and 15 arise from both the [4+2] cycloaddition and the usual Schenck ene reaction pathways. This special diene reactivity of the isoquinolinone system towards singlet oxygen is further interpreted by frontier molecular orbital (FMO) interaction considerations.
Ling, Ke-Qing,Ye, Jia-Hai,Chen, Xian-Yang,Ma, De-Jian,Xu, Jian-Hua
p. 9185 - 9204
(2007/10/03)

Dry reaction on KF-alumina: Synthesis of 4-arylidene-1,3-(2H,4H) isoquinolinediones
1,2,3,4-Tetrahydroisoquinoline-1,3-dione (1) and arylcarboxyaldehydes (2) were condensed to 3-(arylmethylene)-1,2,3,4-tetrahydroisoquinoline-1,3- dione (3) in presence of potassium fluoride on alumina without solvent under focused microwave irradiation.
Villemin, Didier,Martin, Benoit,Khalid, Mohamed
p. 3195 - 3200
(2007/10/03)

ARYLIDENE-HETEROCYCLIC DERIVATIVES AND PROCESS FOR THEIR PREPARATION
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(2008/06/13)

Annulation Reactions of 3-Aminoisoquinolin-1(2H)-one. Synthesis of Pyrimidoisoquinolines, Pyridoisoquinolines and Pyrroloisoquinolines
Reactions of the title compound with the malonic acid derivatives diethyl ethoxymethylenemalonate (EMME), ethyl ethoxymethylenecyanoacetate (EMCA) and ethoxymethylenemalononitrile (EMMN) are reported.Condensations occur at the amino group or C-4, depending on conditions and the former intermediate was successfully cyclized to the pyrimidoisoquinoline system.Reactions with 2,4-pentanedione and p-bromophenacyl bromide gave only the angular systems, pyridoisoquinoline and pyrroloisoquinoline, respectively.
Deady, Leslie W.,Quazi, Nurul H.
p. 793 - 796
(2007/10/02)

Incorporation of Molecular Nitrogen Into Organic Compounds. Titanium Catalyzed Nitrogenation
Incorporation of molecular nitrogen into organic compounds was realized using a catalytic amount of TiCl4 in the presence of excess TMSCl and Li.Various imides were prepared from the corresponding acid anhydrides by use of this catalytic system.
Mori, Miwako,Kawaguchi, Mami,Hori, Masanori,Hamaoka, Shin-ichi
p. 729 - 740
(2007/10/02)

INCORPORATION OF MOLECULAR NITROGEN INTO AMIDES AND IMIDES BY USE OF TITANIUM-NITROGEN COMPLEXES
Molecular nitrogen was incorporated into amides and imides by the reaction of titanium-nitrogen complex 1 prepared from TiCl3 and Mg under N2 in THF with acyl chlorides 3.The cyclic imides 10, 12, 14 and quinazoline 16 were obtained by the reaction of isocyanate complex 6 generated by fixation of CO2 into titanium complex 1 with the corresponding cyclic anhydrides 9, 11, 13 and benzoxazone 15.
Mori,Miwako,Uozumi, Yasuhiro,Shibasaki, Masakatsu
p. 6187 - 6190
(2007/10/02)

Heterocyclic Imines and Amines. Part 19. Isoquinoline and Other Products from α,o-Dicyanostilbene and Basic Reagents
α,o-Dicyanostilbene (1) was cleaved by hydrazine or hydroxylamine under mildly acid conditions to o-cyanobenzyl cyanide (2) and benzaldehyde, isolated as derivatives.Sodamide with compound (1) gave 1-amino-4-cyano-3-phenylisoquinoline: alkoxides similarly gave the 1-alkoxy compounds, the presumed intermediate 3,4-dihydroisoquinoline from the methoxide reaction being isolated and separately dehydrogenated.Acid hydrolysis of the 1-ethoxy compound gave the known 4-cyano-3-phenylisoquinolin-1(2H)-one.With the anion of o-cyanobenzyl cyanide, compound (1) gave a 1-amino-4-cyano-3-(2-substituted phenyl)isoquinoline, which was oxidised to 1-amino-4-cyano-3-(2-carboxyphenyl)isoquinoline.The latter lost water at 210 deg C to give yellow 12-cyano-5-iminoisoindoloisoquinolin-7(5H)-one, closely related to known compounds.
Barnard, Ian F.,Elvidge, John A.
p. 1813 - 1818
(2007/10/02)

Syntheses of Fluorescent Dyes, 10. - 2-Substituted Pyranoisoquinoline-3,6-diones and Merocyanine Dyes from Homophthalimides
The homophthalimides 1a-c were condensed with trimethoxymethane in the presence of acetic anhydride to give the enol ethers 2a-c, whereas the reaction of 1a-d with trimethoxymethane and arylamines (or N-methylurea in the case of 3c) affords the enamines 3
Wolfbeis, Otto S.,Trummer, Iris,Knierzinger, Andreas
p. 811 - 818
(2007/10/02)

A PREFERRED METHOD FOR IMIDE PREPARATION
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Crockett, Geoffrey C.,Swanson, Barry J.,Anderson, David R.,Koch, Tad H.
p. 447 - 454
(2007/10/02)

Isoquinolones: Part IV - Synthesis of 3-Methylisoquinolone-4-carboxylic Acids and Action of Ammonia and Aqueous Methyl Amine on 3-Methylisocoumarin-4-carboxylic Acid Esters
Ammonia reacts with 3-methylisocoumarin-4-carboxylic acid ester (II) on a boiling water-bath to give homophthalimide (III, R'=H) and 3-methylisoquinolone-4-carboxylic acid ester (IV) in nearly equal amounts.At room temperature ammonia reacts to give IV as the major product in good yield.Aq. methyl amine, however, reacts with II to give N-methylhomophthalimide (III, R'=Me) as the major product along with small amounts of compound VI (R1=Me) and some unchanged isocoumarin.Formation of the various products has been rationalised.
Datta, D.,Tirodkar, R. B.,Usgaonkar, R. N.
p. 641 - 643
(2007/10/02)