Cyclopropanedicarboxylic Acid Research Articles

Preparation, characterization and crystal structures of metal(II) tetraza macrocyclic complexes with organic co-ligands

The complexes [Ni(L1)(pyc)2]·2H2O (1) (L1 = C-meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane; Hpyc = pyrazinecarboxylic acid) and [Cu(L2)(H-cpdc)] (2) (L2 = 3,14-dimethyl-2,6,13,17-tetraazatricyclo[14,4,01.18,07.12]docosane; H2-cpdc = cyclopropanedicarboxylic acid) have been synthesized and structurally characterized. The crystal structure of complex 1 shows a distorted octahedral coordination geometry around the nickel(II) center, with four secondary amines in the equatorial positions and two nitrogen atoms of the pyc− ligands in the trans positions. In complex 2, the coordination environment around the copper(II) center is a Jahn–Teller distorted octahedron with four Cu–N bonds and two axial Cu–O bonds. The electronic spectra, electrochemical and TGA behavior of the complexes are significantly affected by the nature of the axial pyc− and H-cpdc− ligands.

Wheel-like Ln18 Cluster Organic Frameworks for Magnetic Refrigeration and Conversion of CO2

Two isostructural 2D MOFs ([Ln7(CDA)6(HCOO)3(μ3-OH)6(H2O)8] n, abbreviated as 1-Gd and 2-Dy) were successfully synthesized under solvothermal conditions. The self-assembly of lanthanide(III) nitrate and 1,1'-cyclopropane-dicarboxylic acid (H2CDA) resulted in wheel-like Ln18 cluster second building units (SBU), which are further linked to six neighboring wheels to generate a 2D ordered honeycomb array. Both 1-Gd and 2-Dy exhibit high thermal stability and decompose above 330 °C. Moreover, they have good solvent stability in ten common solvents and pH stability with pH values from 1 to 13. Magnetic studies reveal that 1-Gd exhibits weak antiferromagnetic coupling between adjacent Gd3+ ions and has a large magnetocaloric effect of 47.30 J kg-1 K-1 (Δ H = 7.0 T at 2 K), while 2-Dy shows ferromagnetic interaction between adjacent Dy3+ ions. Interestingly, 1-Gd and 2-Dy can catalyze the cycloaddition of CO2 to epoxides under mild conditions and can be reused at least five rounds with negligible loss of catalytic performance.

Three coordination polymers based on M2 (M = Co, Ni and Zn) clusters: Structures, magnetic and fluorescent properties

Three new coordination polymers, [M2(CDA)2(EG)2]n (M=Co (1), Ni (2) and Zn (3), H2CDA=1,1′-cyclopropane-dicarboxylic acid and EG=ethylene glycol), have been synthesized under solvothermal conditions and characterized via single-crystal X-ray diffraction, PXRD, EA, FT-IR, and TGA. Structural analysis indicates that metal ions form M2 clusters through μ2-O, which are further linked by CDA2− to generate 2D sheet structure with sql topology. The EG molecule functions not only as solvent but also as the chelate ligand. Magnetic measurements of complexes 1 and 2 have been carried out, which indicate the existence of metamagnetic behavior in complex 1 and antiferromagnetic interaction in complex 2. Furthermore, the fluorescence property of complex 3 was investigated.

1D hydrogen-bonded infinite chains from tetraaza macrocycle nickel(II) complexes and ligands

The reaction of square planar complex [Ni(L2)]Cl2·2H2O (L2=3,14-diethyl-2,6,13,17-tetraazatricyclo[14,4,01.18,07.12]docosane) with ligands KNCS and H2cpdc generates 1D hydrogen-bonded infinite chains [Ni(L2)(NCS)2] (1) and [Ni(L2)(H-cpdc)2] (2) (H2cpdc=cyclopropanedicarboxylic acid). These compounds have been characterized by X-ray crystallography, spectroscopic, cyclic voltammetry and thermogravimetry. The crystal structures of compounds 1 and 2 show that each nickel(II) centre has an elongated distorted octahedral geometry with the axial ligands. Electronic spectra and redox potentials of the complexes 1 and 2 exhibit a high-spin octahedral environment, which is reflected by the nature of the axial ligands. The TGA behaviors of two compounds 1 and 2 are also significantly affected by the nature of the axial ligands.

Cyclopropane derivatives as potential human serine racemase inhibitors: unveiling novel insights into a difficult target

d-Serine is the co-agonist of NMDA receptors and binds to the so-called glycine site. d-Serine is synthesized by human serine racemase (SR). Over activation of NMDA receptors is involved in many neurodegenerative diseases and, therefore, the inhibition of SR might represent a novel strategy for the treatment of these pathologies. SR is a very difficult target, with only few compounds so far identified exhibiting weak inhibitory activity. This study was aimed at the identification of novel SR inhibitor by mimicking malonic acid, the best-known SR inhibitor, with a cyclopropane scaffold. We developed, synthesized, and tested a series of cyclopropane dicarboxylic acid derivatives, complementing the synthetic effort with molecular docking. We identified few compounds that bind SR in high micromolar range with a lack of significant correlation between experimental and predicted binding affinities. The thorough analysis of the results can be exploited for the development of more potent SR inhibitors.

SYNTHESIS AND PHARMACOLOGICAL EVALUATION: ANTIMICROBIAL, ANTI-INFLAMMATORY, ANALGESIC, ULCEROGENIC PROPERTIES OF SEVERAL BIS-HETEROCYCLIC DERIVATIVES

In Medicinal chemistry, heterocyclic derivatives contributed the largest classical division of organic chemistry. Thiadiazole compounds have been know many biological activities such as hypoglycemic, anticancer, anti-inflammatory, anti-asthmatic, antihypertensive and etc. On this research, several 1,1- Bis [2-{2-(5-(arylidene)imino-1,3,4-thiadiazol-2-yl) methyl amino}- 1,3,4-thiadiazo-5-yl] cyclopropane 5(a-h) have been synthesized from cyclopropane dicarboxylic acid comprising thiadiazole moieties. All the synthesized compounds have been characterized by elemental (C,H,N) and spectral (I.R., 1 H- NMR, Mass) analysis. Furthermore, all synthesized compounds were screened for their antifungal, antimicrobial, anti-inflammatory, analgesic, ulcerogenic and toxic activities. The Compound 5f , 3-chlorophenyl substituted was found the most potent in antimicrobial spectrum against all the used microbes. On the other hand, compound 5 g, 4-hydroxy-3-methoxy phenyl substituted was found the most potent in anti-inflammatory, analgesic, and ulcerogenic activities which further evaluated for lesser toxicity test. Key words : Bis -phenylarylidinylthiadiazolidinone cyclopropane, anti-microbial, anti-inflammatory, analgesic, ulcerogenic and toxicity studies

Studies on Some Bioactive 1,1-Bis(2-benzylidene-5-aryliden-1,3-thiadiazolidin-4-one)cyclopropane

Some novel heterocyclic derivatives of 1,1-bis(2-phenyl-5-arylidine-1,3-thiadiazolidin-4-one)cyclopropane 4(a-i) have been synthesized from cyclopropane dicarboxylic acid and substituted thiadiazole moieties. All the synthesized compounds have been characterized by elemental and spectral (I.R., <TEX>$^1H$</TEX>-NMR, Mass) analysis. Furthermore, above said compounds were screened for their antifungal and antibacterial activities. Compound 4c was found the most potent one which further evaluated for lesser toxicity test.

Synthesis of 4-substituted 3-oxabicyclo[3.1.0]hexan-2-one

Cyclopropanedicarboxylic acid anhydride can be converted to 4-substituted 3-oxabicyclo-[3.1.0]hexan-2-one by reaction with Grignard reagents in ether or tetrahydrofuran solution.

Synthesis of Thiadiazoles and 1,2,4-Triazoles Derived from Cyclopropane Dicarboxylic Acid

New heterocyclic derivatives of cyclopropane dicarboxylic acid comprising thiadiazole and 1,2,4-triazole moieties are reported. Reaction of 1,1-cyclopropane dicarboxylic acid (1) with thiosemicarbazide and phosphorous oxychloride resulted in 1,1-bis (2-amino-1,3,4-thiadiazol-5- yl)cyclopropane (2). Cyclopropane dicarboxylic acid thiosemicarbazide (6) was converted into 1,1-bis(3-thio-4H-1,2,4-triazol-5-yl) cyclo- propane (7) by ring closure in an alkaline medium. The thiadiazole 2 and the triazole 7 were converted into a variety of derivatives.

Mg-Al 3:1 hydrotalcite catalyst in the synthesis of cyclopropane carboxylic acid derivatives

The non-activated Mg-Al 3:1 hydrotalcite is a suitable basic catalyst both in the intramolecular cyclization reaction of malonic acid allylic esters into bicyclic cyclopropane carboxylic acid lactones and the intermolecular cyclization reaction of dibromoethane and diethyl malonate into cyclopropane dicarboxylic acid diester. The optimal reaction conditions of the intramolecular cyclization were determined using a 2 4 factorial design. An interesting effect on the diastereoselectivity of the intramolecular cyclization was observed compared with the diastereoselectivity of this cyclization using solid potassium carbonate as base.

A Novel Synthesis of 1-Aminocyclopropane-1-carboxylic Acid (ACC)

A novel synthetic route of 1-aminocyclopropane-1-carboxylic acid (ACC) has been built via cyclopropanedicarboxylic acid monohydrazide III in moderation to good yield.

ChemInform Abstract: Efficient Method for Removal of a Carboxylic Acid Moiety from Sterically Crowded Cyclopropanedicarboxylic Acid Derivatives.

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Efficient Method for Removal of a Carboxylic Acid Moiety from Sterically Crowded Cyclopropanedicarboxylic Acid Derivatives

Abstract A versatile method was developed to the dealkoxycarbonylation of sterically crowded cyclopropanecarboxylic acid derivatives via a nonhydrolytic ester cleavage followed by a Barton-type decarboxylation.

ChemInform Abstract: Novel Syntheses of γ‐Selenobutyrates from Geminally Diactivated Cyclopropane Derivatives.

AbstractThe cyclopropanedicarboxylic acid derivatives (I) are cleaved with the reagents (II) or (IV) ‐ (VI), yielding the 2‐(methylselenenylalkyl)malonic ester derivatives (III).

Polyhydrazido acids and polyamidoimides with phenyl and cyclo-propane groups in chain

Properties of some polyhydrazido-acids in DMF and DMF-water solutions and their transformations under the influence of an acetic anhydride-pyridine mixture have been investigated. The polyhydrazido-acids have been obtained from the dihydrazide of (-) (1R,2R) trans-1,2 cyclopropanedicarboxylic acid and the dianhydride of pyromellitic (PHA-I) or 3,3′, 4,4′-diphenyloxide tetracarboxylic (PHA-II) acids and from a model hydrazido acid (MHA) prepared from the same hydrazide and phthalic anhydride. Cooperative changes in the molar rotation [π] and [η] were found in a mixed DMF-water solvent when the solvent composition was varied. These changes are related to intramolecular cooperative conformational transitions of the coil-compact particle type. PHA-II and MHA are used as examples showing that, under the influence of an acetic anhydride-pyridine mixture, cyclodehydration occurs via the formation of amidoisoimide which is isomerized further to amidoimide. When the acetic anhydride-pyridine mixture is present in large excess, the process ends with the acetylation of an amide group adjacent to the three-membered ring.

Three-membered ring formation reaction [I] cyclopropanedicarboxylic acid ester from methyl α-chloroacrylate and ethylzinc chloride

Three-membered ring formation reaction [I] cyclopropanedicarboxylic acid ester from methyl α-chloroacrylate and ethylzinc chloride

Three-membered ring formation reaction [II] asymmetric synthesis of the cyclopropanedicarboxylic acid ester from methyl α-chloroacrylate with ethylzinc chloride

Three-membered ring formation reaction [II] asymmetric synthesis of the cyclopropanedicarboxylic acid ester from methyl α-chloroacrylate with ethylzinc chloride

Synthesis of optically active polymers from propylenediamine and cyclopropanedicarboxylic acid

Synthesis of optically active polymers from propylenediamine and cyclopropanedicarboxylic acid