49705-66-0

Basic information

• Product Name: 2-(4-CHLORO-2-BUTENYL)-1,3-ISOINDOLINEDIONE
• Synonyms: 2-(4-CHLORO-2-BUTENYL)-1,3-ISOINDOLINEDIONE;TRANS-N-(4-CHLOROBUTENYL) PHTHALIMIDE
• CAS NO: 49705-66-0
• Molecular Formula: C₁₂H₁₀ClNO₂
• Molecular Weight: 235.67
• Mol File: 49705-66-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-CHLORO-2-BUTENYL)-1,3-ISOINDOLINEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLORO-2-BUTENYL)-1,3-ISOINDOLINEDIONE(49705-66-0)
• EPA Substance Registry System: 2-(4-CHLORO-2-BUTENYL)-1,3-ISOINDOLINEDIONE(49705-66-0)

Safety Data

• Hazardous Substances Data: 49705-66-0(Hazardous Substances Data)

Usage

Chemical Family

2-(4-chloro-2-butenyl)-1,3-isoindolinedione belongs to the family of isoindolinediones.

Physical Form

It is a crystalline solid.

Color

It has a pale yellow color.

Solubility

It is soluble in organic solvents.

Uses

It is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals.

Medicinal Properties

It has been studied for its potential anti-inflammatory and analgesic properties, making it an important target for medicinal chemistry research.

Toxicity

It is known to be toxic and may cause irritation upon contact with skin or eyes.

Upstream product

• 136918-14-4 phthalimide 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 1074-82-4 2,3-dihydro-1H-isoindole-1,3-dione potassium 
• 1074-82-4 potassium phtalimide 
• 764-41-0 1,4-dichloro-2-butene 

Downstream Products

• 121030-30-6 3-Butyl-3-hydroxy-2-((2E,4E)-5-phenyl-penta-2,4-dienyl)-2,3-dihydro-isoindol-1-one 
• 77629-06-2 (2Z,4E)-5-phenyl-1-(N-phthalimido)-2,4-pentadiene 
• 77629-05-1 2-((2E,4E)-5-phenylpenta-2,4-dien-1-yl)isoindoline-1,3-dione 
• 121030-17-9 (2Z)-4-cyclohexylidene-1-(N-phthalimido)-2-butene 
• 121030-10-2 (2E)-4-cyclohexylidene-1-(N-phthalimido)-2-butene 
• 121030-13-5 (2Z,4E,6E)-7-phenyl-1-(N-phthalimido)-2,4,6-heptatriene 
• 121030-06-6 (2,E,4E,6E)-7-phenyl-1-(N-phthalimido)-2,4,6-heptatriene 
• 121055-36-5 (2Z,4E)-5-(4'-chlorophenyl)-1-(N-phthalimido)-2,4-pentadiene 
• 121030-04-4 (2E,4E)-5-(4'-chlorophenyl)-1-(N-phthalimido)-2,4-pentadiene 
• 121030-11-3 (2Z,4E)-5-(4'-methoxyphenyl)-1-(N-phthalimido)-2,4-pentadiene 
• 121030-03-3 (2E,4E)-5-(4'-methoxyphenyl)-1-(N-phthalimido)-2,4-pentadiene 
• 675599-75-4 2-[(E)-4-[4-(2,3-dichlorophenyl)piperazin-1-yl]but-2-enyl]isoindoline-1,3-dione 
• 1875-48-5 N-aminophthalamide 

Relevant articles and documents

Compound with dopamine D3 receptor adjusting activity, and applications thereof

The invention relates to a compound with dopamine D3 receptor adjusting activity, and applications thereof, and more specifically discloses dopamine receptor D3R as a novel target of post-traumatic stress disorder (PTSD) in prevention, treatment/or auxiliary treatment of PTSD, and screening of anti-PTSD medicines, and relates to applications of a compound with dopamine receptor D3R adjusting activity in preparation of medicines used for preventing, treatment and/or auxiliary treatment of PTSD.

Design, Synthesis, Structure-Activity Relationship Studies, and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Modeling of a Series of O-Biphenyl Carbamates as Dual Modulators of Dopamine D3 Receptor and Fatty Acid Amide Hydrolase

We recently reported molecules designed according to the multitarget-directed ligand paradigm to exert combined activity at human fatty acid amide hydrolase (FAAH) and dopamine receptor subtype D3 (D3R). Both targets are relevant for tackling several types of addiction (most notably nicotine addiction) and other compulsive behaviors. Here, we report an SAR exploration of a series of biphenyl-N-[4-[4-(2,3-substituted-phenyl)piperazine-1-yl]alkyl]carbamates, a novel class of molecules that had shown promising activities at the FAAH-D3R target combination in preliminary studies. We have rationalized the structural features conducive to activities at the main targets and investigated activities at two off-targets: dopamine receptor subtype D2 and endocannabinoid receptor CB1. To understand the unexpected affinity for the CB1 receptor, we devised a 3D-QSAR model, which we then prospectively validated. Compound 33 was selected for PK studies because it displayed balanced affinities for the main targets and clear selectivity over the two off-targets. 33 has good stability and oral bioavailability and can cross the blood-brain barrier.

NOVEL DOPAMINE D3 RECEPTOR LIGANDS, THE PREPARATION AND USE THEREOF

The invention discloses novel piperazine derivatives represented by formula I having activity for modulating dopamine D3 receptor, their stereoisomers, pharmaceutical salts, solvates, and the pharmaceutical compositions containing such compounds, their preparation and the use of such compounds for preventing or treating the diseases correlated with central nervous system disorder, such as Parkinson's disease, schizophrenia, drug addiction and relapse and the like, as well as the use of such compounds for kidney protection and immune modulation, or as implemental medicine for researching the function of D3R and the diseases correlated with disorder of D3R function.

NOVEL DOPAMINE D3 RECEPTOR LIGANDS AND PREPARATION AND MEDICAL USES OF THE SAME

The present invention relates to a novel piperazine derivative represented by Formula I having an activity for regulating dopamine D3 receptor, stereoisomers thereof, pharmaceutically acceptable salts or solvates, and a pharmaceutical composition comprising the compound, a process for preparing the same, and use thereof in the prevention or treatment of a disease associated with central nervous system dysfunction, such as Parkinson''s disease, schizophrenia, drug addiction and relapse, as well as kidney protection and immunoregulation, or as a tool for researching D3R function or diseases associated with D3R dysfunction.

Structurally rigid dopamine d3 receptor selective ligands and process for making them

A family of structurally rigid dopamine D3 receptor selective ligands is described. The family of structurally rigid dopamine D3 receptor selective ligands has the formula wherein A is cis or trans —CH═CH—, —C═C—, or cyclohexyl. B is cis or trans —CH═CH—

COMBINATION THERAPY WITH INHIBITORS OF INDUCIBLE NITRIC OXIDE SYNTHASE AND ALKYLATING AGENTS

A combination therapy comprising administration of a carbamoylating chemotherapeutic agent in conjunction with administration of a selective iNOS inhibitor compound is disclosed. Optionally, resection and radiation therapy are provided with the therapeutic combination. A medicament comprising a carbamoylating chemotherapeutic agent and a selective iNOS inhibitor compound together with a pharmaceutically acceptable carrier is further disclosed. A kit comprising a carbamoylating chemotherapeutic agent and a selective iNOS inhibitor compound is further disclosed.

The impact of spacer structure on 5-HT7 and 5-HT1A receptor affinity in the group of long-chain arylpiperazine ligands

New cis-, trans-2-butene and 1,2-bismethylbenzene analogues of MM77 and NAN-190 (1-{4-[4-(2-methoxyphenyl)-piperazin-1-yl]-butyl}-pyrrolidine-2,5-dione and isoindole-1,3-dione, respectively) were synthesized. The differences in their in vitro affinity for serotonin 5-HT7 and 5-HT1A receptors were explained using a conformational analysis. A bioactive conformation of those compounds for the 5-HT7 receptor, different from that established for 5-HT1A, was proposed.

METHODS FOR TREATMENT AND PREVENTION OF GASTROINTESTINAL CONDITIONS

Therapeutic methods for the prevention ad treatment of conditions and diseases of the gastrointestinal tract involving an overproduction of nitric oxide by inducible nitric oxide synthase are described, the methods including administering to a subject in need thereof a therapeutically effective amount of a selective inhibitor of inducible nitric oxide synthase (iNOS). The methods also include the use of selective inhibitors of iNOs in combination with other therapeutic agents, including antimicrobial agents and antisecretory agents.

N-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl, butenyl and butynyl}arylcarboxamides as novel dopamine D3 receptor antagonists

The dopamine D3 receptor subtype has been targeted as a potential neurochemical modulator of the behavioral actions of psychomotor stimulants, such as cocaine. Previous synthetic studies provided structural requirements for high affinity bindin

Inhibition of bovine plasma amine oxidase by 1,4-diamino-2-butenes and -2-butynes

Bovine plasma amine oxidase (BPAO) was previously shown to be irreversibly inhibited by propargylamine and 2-chloroallylamine. 1,4-Diamine versions of these two compounds are here shown to be highly potent inactivators, with IC50 values near 20 μM. Mono-N-alkylation or N,N-dialkylation greatly lowered the inactivation potency in every case, whereas the mono-N-acyl derivatives were also weaker inhibitors and enzyme activity was recoverable. The finding that the bis-primary amines 1,4-diamino-2-butyne (a known potent inhibitor of diamine oxidases) and Z-2-chloro-1,4-diamino-2-butene are potent inactivators of BPAO is suggestive of unexpected similarities between plasma amine oxidase and the diamine oxidases and implies that it may be unwise to attempt to develop selective inhibitors of diamine oxidase using a diamine construct.