Cyclobutanedicarboxylic Acid Research Articles

Polyphenolic truxillic acid crosslinked sodium alginate film with notable antimicrobial and biodegradable properties for food packaging

This work demonstrated an innovative antimicrobial and biodegradable food packaging film CBDA-10-SA which was prepared by crosslinking a natural polyphenolic truxillic acid (cyclobutane-dicarboxylic acid, CBDA-10) and sodium alginate (SA). The CBDA-10-SA film exhibited improved tensile strength (148 MPa) and UV shielding capabilities. The maximum thermal decomposition temperature was achieved of 249 °C. Compared to SA film, CBDA-10-SA showed increased antibacterial activities. In food packaging test, the CBDA-10-SA inhibited the rapid growth of potential of hydrogen (pH) value, slowed down the weight loss, reduced total plate count (TPC) value of pork, and delayed the spoilage process of pork. Notably, CBDA-10-SA displayed remarkable degradability in soil, with 60 % degrading in four weeks. In this study, CBDA-10-SA showed enhanced physicochemical and mechanical properties compared to traditional SA film. Those improvements make it anticipated to be used in not only food packaging but also mechanical, pharmaceutical, and agricultural fields.

Aminoguanidinium hydrogen 1,1-cyclobutane dicarboxylate: Synthesis, structural characterization and molecular docking studies

On neutralization of Aminoguanidine bicarbonate (H2Agun) with 1,1 -cyclobutane dicarboxylic acid (H2CBD) resulted aminoguanidinium salt, [(HAgun)+(HCBD)-]. Using FT-IR, 1H NMR, 13C NMR, and analytical spectroscopy, the compound was identified and characterized. Furthermore, single X-ray diffraction experiment confirms the molecular structure of the salt. The molecular docking approach has been employed to investigate the inhibitory properties of aminoguanidinium hydrogen 1,1-cyclobutane dicarboxylate on three key cancer protein receptors: 3WZE (VEGFR kinase), 5ZMA (crystal structure of an allosteric Eya2 phosphates inhibitor lung cancer protein), and 1JNX (BRCT repeat region from the breast cancer associated protein). Observation of lower binding energy of −4.67 kcal/mol for 3WZE, −4.57 kcal/mol for 5ZMA and 1.7 kcal/mol for 1JNX, respectively, indicating high stability with the protein molecule.

Phytochemical study of Alzatea verticillata, the sole species belonging to the Alzateaceae family

Alzatea verticillata Ruiz & Pav. (Alzateaceae) is a tropical tree from Central and South America. It is the only living species of Alzatea genus and the Alzateaceae family, all others being extinct. With the aim to investigate the possibility to find unusual natural products, the chemical content of the dichloromethane and methanolic extracts (stems and leaves) of A. verticillata have been investigated. Apolar and polar extracts were purified by semi-preparative HPLC using appropriate stationary phase columns allowing the isolation of 12 compounds: walterolactone B (2) walterolactone A/B β-D-pyranoglucoside (3), gallic acid (4), caffeic acid 4-O-β-D-glucopyranoside (6), walterolactone A/B 6-O-gallate-β-D-glucopyranoside (8), caffeic acid (9), 8-desmethylsideroxylin (11), sideroxylin (12) and 7,7′-bis(3,4-dihydroxyphenyl)-8,8′-cyclobutanedicarboxylic acid (7). Three isolated compounds are natural products described here for the first time: dimethyl-anemonin (1) and two β-truxinic acid derivatives (rel-(7S, 8R, 7′R, 8′S)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane dicarboxylic acid (5) and rel-(7S, 8R, 7′R, 8′S)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane-9-methyl dicarboxylic acid (10). The structures of the isolated compounds were elucidated by NMR and HRMS. The structure of compound 1 was confirmed by X-ray crystallography. A MS-based metabolite analysis of the A. verticillata extracts revealed additional truxinic acid derivatives that were putatively annotated with the help of feature-based molecular network. The presence of phenolic compounds such as truxinic acid derivatives could explain the traditional use of this plant as these compounds are known to possess anti-inflammatory and anti-nociceptive properties.

Studies on Pd(1,4-bis(2-hydroxyethyl)piperazine)-dicarboxylic acid complexes as models for carboplatin with structural features enhancing the interaction with DNA

[Pd(BHEP)Cl2] and [Pd(BHEP)(CBDA)] complexes, where BHEP = 1,4-bis(2-hydroxyethyl)piperazine and CBDA = cyclobutanedicarboxylate, were synthesized and characterized. [Pd(BHEP) (CBDA)] crystallizes in space group P21, a = 9.5740(8) Å, b = 9.4700(7) Å, c = 9.7890(10) Å, α = 90.00°, β = 113.360(5)°, γ = 90.00°, V = 814.78(13) Å3, Z = 2. The palladium center has a typical square planar geometry with tetrahedral distortion. DFT calculations show good agreement between theoretical and X-ray data. The stability constants and stoichiometry of the complexes formed between various dicarboxylic acids and [Pd(BHEP)(H2O)2]2+ were studied. Dicarboxylic acids form 1:1 and protonated complexes. Inosine forms 1:1, 1:2 and the protonated form of 1:1 complexes. The temperature effect on the formation constant of the cyclobutanedicarboxylate complex was investigated. The hydrolysis of [Pd(BHEP)(H2O)2]2+ and complex formation with cyclobutanedicarboxylic acid are exothermic processes.

A novel class of bis- and tris-chelate diam(m)inebis(dicarboxylato)platinum(IV) complexes as potential anticancer prodrugs.

A novel class of platinum(IV) complexes of the type [Pt(Am)(R(COO)2)2], where Am is a chelating diamine or two monodentate am(m)ine ligands and R(COO)2 is a chelating dicarboxylato moiety, was synthesized. For this purpose, the reaction between the corresponding tetrahydroxidoplatinum(IV) precursors and various dicarboxylic acids, such as oxalic, malonic, 3-methylmalonic, and cyclobutanedicarboxylic acid, was utilized. All new compounds were characterized in detail, using 1D and 2D NMR techniques, ESI-MS, FTIR spectroscopy, elemental analysis, TGA, and X-ray diffraction. Their in vitro cytotoxicity was determined in a panel of human tumor cell lines (CH1, SW480 and A549) by means of the MTT colorimetric assay. Furthermore, the lipophilicity and redox properties of the novel complexes were evaluated in order to better understand their pharmacological behavior. The most promising drug candidate, 4b (Pt(DACH)(mal)2), demonstrated low in vivo toxicity but profound anticancer activity against both the L1210 leukemia and CT-26 colon carcinoma models.

Synthesis of novel β-aminocyclobutanecarboxylic acid derivatives by a solvent-free aza–Michael addition and subsequent ring closure

Novel β-aminocyclobutanecarboxylic acid derivatives were prepared via a sequential solvent-free aza-Michael addition of benzophenone imine across 3-halopropylidenemalonates and base-induced ring closure. These highly substituted cyclobutanedicarboxylic acid derivatives were subjected to a reactivity study which demonstrated the tendency of these donor-acceptor substituted four-membered rings to be converted into their corresponding ring-opened products.

Toward the design of novel polynuclear platinum antitumor complexes: a polydentate ligand system based on dipyridylamine and 1,3,5-trimethylenebenzene.

A novel hexadentate ligand, N,N,N',N',N",N"-hexa(2-pyridyl)-1,3,5-tris(aminomethyl)benzene (L), was designed and synthesized. The X-ray structure analysis reveals that the three dipyridylamine (DPA) groups of L are almost perpendicular to the central trimethylenebenzene, and two of them are spacially close to each other while the third one is further apart. The trinuclear Pt(II) complexes [Pt(3)LCl(6)] (1) and [Pt(3)L(CBDCA)(3)] (2) (where CBDCA represents cyclobutane dicarboxylic acid) were prepared and fully characterized by IR, NMR, and ESMS spectroscopy. A mononuclear complex, [PtL(CBDCA)] (3), was also prepared and structurally characterized, which suggests that controlled formation of mono-, di-, and trinuclear complexes with L is possible. Spectroscopic data showed that complexes 2 and 3 are able to bind to calf thymus DNA and their CBDCA group can be readily replaced by thiourea.

Synthesis and characterization of platinum(II) and (IV) complexes containing hexamethyleneimine ligand: crystal structure of [Pt II(hexamethyleneimine) 2(cyclobutanedicarboxylato)]·H 2O

A series of new platinum(II) and platinum(IV) complexes of the type [Pt II(HMI) 2X] (where HMI=hexamethyleneimine, X=dichloro, sulfato, 1,1-cyclobutanedicarboxylato [CBDCA], oxalato, methylmalonato, or tatronato) and [Pt IV(HMI) 2Y 2Cl 2] (where Y=hydroxo, acetato, or chloro) were synthesized and characterized by infrared (IR) spectroscopy, 13C and 195Pt nuclear magnetic resonance (NMR) spectroscopy and elemental analysis. Among the complexes synthesized, [Pt II(hexamethyleneimine) 2(1,1-cyclobutanedicarboxylato)]·H 2O was examined by single-crystal X-ray diffraction. The slightly distorted square planar coordination environment of the platinum metal includes the amino group of the hexamethyleneimine (HMI) molecule and the oxygen atoms of the carboxylato ligand. The cyclobutanedicarboxylic acid (CBDCA) molecule adopts six-member chelating rings with platinum. Hydrogen bonding plays an important part in holding the crystal lattice together.

Complex formation equilibria of palladium(II) complexes involving N, N′-dimethylethylenediamine, DNA constituents and cyclobutane dicarboxylic acid. The catalysis of glycine methyl ester hydrolysis through complex formation

Mixed-ligand complex formation equilibria of Pd(Me 2en)–CBDCA–DNA constituent have been investigated (Me 2en= N, N′-dimethylethylenediamine, CBDCA=cyclobutane dicarboxylic acid). The results show ring opening of CBDCA and monodentate complexation of the DNA constituent. Stoichiometries and stability constants of the complexes were determined at 25 °C and at constant 0.1 M ionic strength. The kinetics of base hydrolysis of glycine methyl ester in presence of Pd(Me 2en) 2+ complex was studied in aqueous solution at different temperatures, and in dioxane–water solutions of different compositions at 25 °C.

Equilibrium Studies of Mixed Ligand Complexes Involving (1,2-Diaminopropane)-Palladium(II) and Some Bioligands

Complex formation equilibria have been investigated for [Pd(DAP)(H2O)2]2+ (DAP=1,2-diaminopropane) with Cl−, OH−, cyclobutanedicarboxylic acid (CBDCAH2), amino acids, peptides, and DNA units. Stoichiometries and stability constants of the complexes were determined at 25°C and constant ionic strength (0.1 M NaNO3). The results showed the formation of 1:1 complexes with amino acids and CBDCAH2. Peptides formed both 1:1 complexes and the corresponding deprotonated amide species. DNA constituents formed both 1:1 and 1:2 complexes. Pd(DAP)(CBDCA)ċH2O was isolated and characterized. The concentration distribution of the complexes in solution was evaluated.

Equilibrium studies of complex formation involving palladium(II)-(1,3-diaminopropane) and cyclobutane dicarboxylic acid, DNA units, amino acids or peptides

Complex formation equillibria of [Pd(DAP)(H2O)2]2+ (DAP = 1,3-diaminopropane) with Cl−, OH−, cyclobutane dicarboxylic acid (CBDCA), amino acids, peptides and DNA unit constituents have been investigated. Stoichiometries and stability constants of the complexes were determined at 37°C and 0.16 M NaNO3 ionic strength. The results showed the formation of 1:1 complexes with amino acids and CBDCA. Peptides form both 1:1 complexes and the corresponding deprotonated amide species. DNA constituents form both 1:1 and 1:2 complexes. [Pd(DAP)(CBDCA)] was isolated and characterized. The concentration distribution of the complexes in solution was evaluated.

ChemInform Abstract: Efficient Preparation and Resolution of trans‐1,2‐ Cyclobutanedicarboxylic Acid and Some of Its Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis, antitumor activity, and chemical properties of silaplatin and related platinum (II) and platinum (IV) complexes derived from beta-silyl amines.

Platinum (II) and platinum (IV) coordination complexes derived from beta-silyl-substituted amines were prepared. The solubility of selected complexes in water and physiological saline was measured, and the effect of the beta-silicon on the reactivity of the complex in aqueous solution was determined by HPLC. The stabilities of selected silyl complexes were compared to the carbon analogues. The cyclic complexes 2a ("silaplatin") and its Pt(IV) analogue, 2b, were very active against L1210 leukemia in vivo. Both the platinum (II) complex 2a and the platinum (IV) complex 2b produced a significant number of cures over the dose range 10-40 mg/kg. The platinum (II) complex 2a, silaplatin, was very active in vivo against an L1210 leukemia subline that was resistant to cisplatin; 2a was also active, when given ip, against ic implanted L1210. The cyclobutanedicarboxylic acid complex 3c was synthesized; this complex was active against both cisplatin sensitive and resistant L1210 leukemia but was less potent than the analogous dichloro compound 2a. The acyclic platinum (II) and platinum (IV) complexes 1a,b were synthesized and unexpectedly found to be inactive in vivo against L1210 leukemia. More lipophilic silaplatin analogues were prepared--Pt(II) complex 2c and Pt(IV) complex 2d have one additional methylene carbon compared to 2a,b, whereas Pt(II) complex 2e and Pt(IV) complex 2f have two additional methylene carbons. Cyclization of the alkyl groups attached to the silicon gave the spiro bicyclic Pt(II) complexes 10a and 11a and the Pt(IV) complexes 10b and 11b.

Formation of substituted truxillic and truxinic acids in plant cell walls—a rationale

The formation of phenolic cyclobutane dicarboxylic acids (truxillic and truxinic acids) in plant cell wall materials was investigated using model compounds. Two possible mechanisms were considered—cyclodimerization initiated by light or by a free radical process. Diesters formed by reaction of cinnamic acid with a series of diols had a range of distances separating the double bonds and, upon irradiation with ultraviolet light, gave dimerization products. Dimerization did not occur when peroxidase was added to the diesters to mimic phenolic coupling reactions leading to the formation of lignin in vivo. A minimum separation of two cinnamyl moieties and an optimal relative orientation was observed which can be used to predict substitution patterns for unsaturated phenolic residues on the sugar backbone in plant cell walls.

ChemInform Abstract: Methylene Rocking in Cyclobutanedicarboxylic Acid at 4.2 K. The Geometry of a Four‐Membered Ring in Its Ground State

ChemInformVolume 21, Issue 41 Physical Organic Chemistry ChemInform Abstract: Methylene Rocking in Cyclobutanedicarboxylic Acid at 4.2 K. The Geometry of a Four-Membered Ring in Its Ground State J. A. VAN ZEE, J. A. VAN ZEE Dep. Chem., Univ. Wash., Seattle, WA 98195, USASearch for more papers by this authorA. L. KWIRAM, A. L. KWIRAM Dep. Chem., Univ. Wash., Seattle, WA 98195, USASearch for more papers by this author J. A. VAN ZEE, J. A. VAN ZEE Dep. Chem., Univ. Wash., Seattle, WA 98195, USASearch for more papers by this authorA. L. KWIRAM, A. L. KWIRAM Dep. Chem., Univ. Wash., Seattle, WA 98195, USASearch for more papers by this author First published: October 9, 1990 https://doi.org/10.1002/chin.199041041Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume21, Issue41October 9, 1990 RelatedInformation

Methylene rocking in cyclobutanedicarboxylic acid at 4.2 K. The geometry of a four-membered ring in its ground state

Methylene rocking in cyclobutanedicarboxylic acid at 4.2 K. The geometry of a four-membered ring in its ground state

ChemInform Abstract: Investigations in the Cyclobutanedicarboxylic Acids Series. Part 9. α‐Truxillic Bis(dialkylaminoalkylamide) Salts Possessing Curare‐Like Activity.

Abstractα‐Truxillic dichloride (I) and the amines (II) yield the bis(dialkylaminoalkylamides) (III), from which hydrochlorides and hydrobromides as well as salts with sulfuric, maleic, and fumaric acids are prepared.

Synthesis of cis‐diamino‐[1,1‐[1‐14C]cyclobutanedicarbonyloxy (2)‐0,0] platinum II

AbstractThe synthesis of the title compound (4) is described. [2‐14C]Diethyl malonate was treated simultaneously with a freshly prepared solution of sodium ethoxide and 1,3‐dibromopropane to give 1 1‐[1‐14C]cyclobutanedicarboxylic acid diethyl ester (1). Treatment with potassium hydroxide saponified the ester leaving the dipotassium salt (2). Conversion of potassium tetrachloroplatinate II with potassium iodide followed by ammonium hydroxide resulted in cis‐diamino‐diiodoplatinum II1 (3). Reaction of (3) with 1,1‐[1‐14C]cyclobutanedicarboxylic acid dipotassium salt in the pressence of silver nitrate resulted in the title compound (4).

ChemInform Abstract: Investigation in the Series of Cyclobutanedicarboxylic Acids. Part 8. Synthesis and Curare Like Activity of Bis Quaternary Salts of α‐Truxillic Acid ω‐Dialkylaminoal‐kylamides.

AbstractDie teilweise bereits früher aus Truxillsäuredichlorid (I) und den Dialkylaminoalkylaminen (II) dargestellten Truxillsäurederivate (III) werden mit Ethyliodid zu den Salzen (IV) quaterniert.

Cyclobutanedicarboxylic acids IX. Salts of bis(dialkylaminoalkylamides) of α-truxillic acid with curariform activity

Cyclobutanedicarboxylic acids IX. Salts of bis(dialkylaminoalkylamides) of α-truxillic acid with curariform activity