89180-99-4

Basic information

• Product Name: 1,2-Cyclopropanedicarbonyl chloride (6CI,7CI)
• Synonyms: 1,2-Cyclopropanedicarbonyl chloride (6CI,7CI)
• CAS NO: 89180-99-4
• Molecular Formula: C₅H₄Cl₂O₂
• Molecular Weight: 166.99006
• Product Categories: ACIDHALIDE
• Mol File: 89180-99-4.mol

Chemical Properties

• Boiling Point: 196.7±33.0 °C(Predicted)
• Appearance: /
• Density: 1.582±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,2-Cyclopropanedicarbonyl chloride (6CI,7CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclopropanedicarbonyl chloride (6CI,7CI)(89180-99-4)
• EPA Substance Registry System: 1,2-Cyclopropanedicarbonyl chloride (6CI,7CI)(89180-99-4)

Safety Data

• Hazardous Substances Data: 89180-99-4(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Pungent

Classification

Chloroformate ester

Uses

a. Building block in organic synthesis
b. Production of pharmaceuticals and agrochemicals
c. Manufacturing of fine chemicals
d. Synthesis of cyclopropane-containing compounds
e. Medicinal chemistry and drug discovery

Reactivity

Highly reactive

Safety precautions

Handle with caution, use in well-ventilated area, wear proper personal protective equipment.

Upstream product

• 3999-55-1 diethyl trans-cyclopropane-1,2-dicarboxylate 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 20561-09-5 diethyl (cis,trans)-1,2-cyclopropanedicarboxylate 
• 1489-58-3 trans-1,2-cyclopropanedicarboxylic acid 

Downstream Products

• 35974-53-9 (+/-)-trans-2-dimethylcarbamoyl-cyclopropanecarboxylic acid 
• 3187-76-6 (trans)-cyclopropane-1,2-diamine dihydrochloride 
• 53187-82-9 (trans-cyclopropane-1,2-diyl)dimethanol 
• 96149-00-7 (1S,2S)-cyclopropane-1,2-dicarboxylic acid bis-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester 

Relevant articles and documents

ALKYLBORONIC ACIDS AS ARGINASE INHIBITORS

Provided are alkylboronic acids as arginase inhibitors represented by formula (I), or a pharmaceutically acceptable salt, stereoisomer, tautomer, or prodrug thereof and a pharmaceutical composition comprising said compounds.

IMIDAZOLIDINONE DERIVATIVES AS INHIBITORS OF PERK

The invention is directed to substituted imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I (I) wherein R1, R2, R3, R4, R5, R6, R7, X, Y1, Y2 and Z are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes, as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt-Jakob Disease, fatal familial insomnia, Gerstmann-Str?ussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Molecular modelling studies, synthesis and biological activity of a series of novel bisnaphthalimides and their development as new DNA topoisomerase II inhibitors

A series of bisnaphthalimide derivatives were synthesized and evaluated for growth-inhibitory property against HT-29 human colon carcinoma. The N,N′-bis[2-(5-nitro-1,3-dioxo-2,3-dihydro-1H-benz[de]-isoquinolin- 2-yl)]propane-2-ethanediamine (9) and the N,N′-Bis[2-(5-nitro-1,3-dioxo-2,3-dihydro-1H-benz[de]-isoquinolin- 2-yl)]butylaminoethyl]-2-propanediamine (12) derivatives emerged as the most potent compounds of this series. Molecular modelling studies indicated that the high potency of 12, the most cytotoxic compound of the whole series, could be due to larger number of intermolecular interactions and to the best position of the naphthalimido rings, which favours π-π stacking interactions with purine and pyrimidine bases in the DNA active site. Moreover, 12 was designed as a DNA topoisomerase II poison and biochemical studies showed its effect on human DNA topoisomerase II. We then selected the compounds with a significant cytotoxicity for apoptosis assay. Derivative 9 was able to induce significantly apoptosis (40%) at 0.1 μM concentration, and we demonstrated that the effect on apoptosis in HT-29 cells is mediated by caspases activation.

CYCLOPROPYL-CONTAINING POLYAMINE ANALOGS AS DISEASE THERAPIES

This disclosure relates to specific polyamine analogs and methods of treating cancer using polyamine analogs. The polyamine analogs have cyclopropyl groups in their internal segments.

Novel bisbenzamidines as potential drug candidates for the treatment of Pneumocystis carinii pneumonia

A series of pentamidine congeners has been synthesized and screened for their in vitro activity against Pneumocystis carinii. Among the tested compounds, bisbenzamidines linked by a flexible pentanediamide or hexanediamide chain (7 and 9) emerged as excep

Synthesis and anti-Pneumocystis carinii activity of conformationally restricted analogues of pentamidine

A series of conformationally restricted analogues of pentamidine in which the flexible central bridge has been replaced by trans-cyclopropyl, phenyl, pyridinyl, piperazinyl or homopiperazinyl groups as conformationally restricted linkers have been synthesized. The anti-Pneumocystis carinii activity of these compounds was evaluated in a cell culture model and the DNA binding affinity was determined by thermal denaturation measurements. At 1 μM, compounds 2, 3, 5, 7, 9 and pentamidine were highly effective and caused total inhibition of P. carinii growth in culture. At 0.1 μM, compounds 2, 5, 7 and 10 were more active than pentamidine with N, N'- bis(4amidinophenyl)piperazine 7 being approximately 15-fold more effective than pentamidine. The most active compounds, 7 and 10, showed strong binding affinities for calf thymus DNA and poly(dA-dT); however, a clear correlation between DNA binding affinity and the in vitro anti-P, carinii activity of these compounds was not observed. The results suggest that the nature of the central linker influences the biological actions of these compounds.

Photodecarbonylation of chiral cyclobutanones

Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (-)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropaneas a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product.