21640-35-7

Upstream product

• 21640-31-3 2-(phenylmethyl)isoquinoline-1,3(2H,4H)-dione 
• 703-59-3 homophthalic anhydride 
• 119-65-3 isoquinoline 
• 620-05-3 iodomethylbenzene 
• 15787-39-0 2-benzylisoquinolin-2-ium iodide 
• 7460-55-1 2-(2-bromoacetyl)benzoic acid methyl ester 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 23277-04-5 2-benzylisoquinolin-2-ium bromide 
• 59168-21-7 2-benzyl-1-(2H)-isoquinoline ketone 
• 521-73-3 isoquinoline-1,3,4-trione 
• 100-44-7 benzyl chloride 
• 6772-61-8 2-(4-benzylphenyl)-3,4-dihydroisoquinolin-1(2H)-one 

Relevant academic research and scientific papers

Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts

The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.

Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones

Herein we describe a very useful application of the readily available trifunctional aromatic ketone methyl-2-(2-bromoacetyl)benzoate in reactions with primary amines. An unexpected in situ air oxidation that follows a cascade process allowed the access to

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,

Iodine-catalyzed oxidative multiple C-H bond functionalization of isoquinolines with methylarenes: An efficient synthesis of isoquinoline-1,3,4(2: H)-triones

An iodine-catalyzed multiple C-H bond functionalization of isoquinolines with methylarenes via a successive benzylic sp3 C-H iodination/N-benzylation/amidation/double sp2 C-H oxidation sequence is developed. This reaction utilizes un

Isoquinoline-1,3,4-trione derivative and preparation method thereof

The invention discloses an isoquinoline-1,3,4-trione derivative and a preparation method thereof. The method is characterized in that the isoquinoline-1,3,4-trione derivative is prepared through a reaction of a 3-amino-4-cyano-2-substituted isoquinoline-1-one derivative used as a substrate and an aqueous solution of tert-butyl hydroperoxide at 60-80 DEG C in an organic solvent with copper salt as a catalyst. The method can be used for obtaining multiple isoquinoline-1,3,4-trione derivatives at a high yield, and has the advantages of mild reaction conditions, simplicity in operation and post-treatment, and suitableness for large-scale production.

Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors

A series of isoquinoline-1,3,4-trione derivatives were identified as novel and potent inhibitors of caspase-3 through structural modification of the original compound from high-throughput screening. Various analogues (2, 6, 9, 13, and 14) were synthesized and identified as caspase inhibitors, and the introduction of a 6-N-acyl group (compound 13) greatly improved their activity. Some of them showed low nanomolar potency against caspase-3 in vitro (for example, for 6k, IG50 = 40 nM) and significant protection against apoptosis in a model cell system. Additionally, compound 13f demonstrated a dose-dependent decrease in infarct volume in the transient MCA occlusion stroke model. The present small-molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.

ISOQUINOLINE -1,3,4-TRIONE, THE SYNTHETIC METHOD AND THE USE THEREOF

The invention relates to various substituted isoquinoline-1,3,4-trione, the synthetic method thereof and the use for treating neurodegenerative diseases, especially as the medicine for Alzhermer's disease, apoplexy and brain ischemic injuries. The compound is represented by the following structure formula: Wherein substituents R1 can be one, two or three groups optionally selected from the group consisting of H; alkyl; hydroxyl; alkyl substituted by the groups including halogen, alkoxyl or hydroxyl; alkoxyl or alkylamino substituted by the groups including halogen, alkoxyl or hydroxyl; C2-C6 alkenyl substituted by oxygen or amine; C3-C6 cycloalkyl; substituted aryl; benzyl; alkanoyl; alkanoyl substituted by the groups including halogen, alkoxyl or hydroxyl; C2-C6 enoyl; C3-C6 cycloalkanoyl; tert-butoxycarbonyl; benzoyl; benzoyl substituted by one, two or three groups including alkylamino; benzylacyl; benzylacyl substituted by one, two or three groups including alkylamino; thienoyl; adamantylcarbonyl; mandeloyl; alkoxyl; alkylamino; cycloalkoxyl; cycloalkylamino; amino; acylamino; alkyloxycarbonyl; cycloalkoxycarbonyl; alkanoylxy; alkanoylamino; cycloalkyanoylxy; cycloalkanoylamino; ureido; urenylene; alkanoyl; nitro; carboxyl; R2 is H; alkyl; alkyl or C1-C4 cycloalkyl substituted by the groups including halogen, alkoxyl or hydroxyl; C2-C6 alkenyl; aryl; substituted aryl; X is H, CH2, NH, O, or S; Y is CH, or N.

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.