O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• amides, coumarins, alicyclic ketones, β-ketophosphonates, α-nitroketones, curcumin, and barbituric acid derivatives [1][2][8][9]. We analyzed a number of Biginelli-type products and publications and concluded that Se-containing DHPMs among the rarest examples and, in addition to this, ketosulfones have

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates

• Deepa Nair,
• Abhishek Tiwari,
• Banamali Laha and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2024, 20, 2016–2023, doi:10.3762/bjoc.20.177

• double Michael addition of γ,δ-unsaturated-β-keto esters or Nazarov reagents with suitable acceptors such as nitroalkenes or alkylideneazalactones [7][8][9][10]. From the perspective of an active methylene containing organic moiety, curcumin and its analogs serve as inexpensive and readily available

• starting materials for cascade/domino reactions. Curcumin is the key component present in turmeric and is responsible for its various biological activities. Turmeric has been used in many forms for potential health benefits and as a traditional spice for centuries [11]. Curcumin exhibits diverse biological

• reactions, especially as a Michael donor at the central methylene carbon, and Michael acceptor at the enone vinyl carbon. Therefore, it would be interesting to develop novel methodologies using curcumin and its non-natural analogs as key starting materials [24]. Because of its multifaceted reactive site

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• ), and interleukin-6 (IL-6) [56][57][58]. The combination of crocins with doxorubicin and curcumin also showed a good anti-inflammation effect [56][59]. Antidepression Alsanie et al. found that the therapeutic effect of C. sativus extract on mild and moderate depressive disorder is comparable to

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• curcumin or (iso)quercetin, not to mention hydroxychloroquine. Past these rather scathing comments which could lead to a long-delayed but healthy debate in the concerned countries, the last four decades saw several “revolutions” in medicinal chemistry which were triggered by the following major advance in

• experiments following the screening of a library [51][52]. However, many of these compounds, often of natural origin [53]; polyphenols and curcumin being emblematic [54], are the bread and butter of quack medicine. Indeed, these will be found active on many biochemical or cellular assays [46] and will thus

Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

• Henning Weiss,
• Jeannine Reichel,
• Helmar Görls,
• Kilian Rolf Anton Schneider,
• Mathias Micheel,
• Michael Pröhl,
• Michael Gottschaldt,
• Benjamin Dietzek and
• Wolfgang Weigand

Beilstein J. Org. Chem. 2017, 13, 2264–2272, doi:10.3762/bjoc.13.223

• .13.223 Abstract Eight difluoroboron complexes of curcumin derivatives carrying alkyne groups containing substituents have been synthesized following an optimised reaction pathway. The complexes were received in yields up to 98% and high purities. Their properties as fluorescent dyes have been

• investigated. Furthermore, a strategy for the hydrolysis of the BF2 group has been established using aqueous methanol and sodium hydroxide or triethylamine. Keywords: BF2 complex; curcumin; dyes; fluorescence; hydrolysis; spectroscopy; Introduction In recent years curcumin, a pigment naturally occurring in

• diseases and having only negligible side effects, low water solubility and fast degradation limit their potential medical application to this day [7]. The formation of the curcumin structure motif takes place by a base catalysed aldol condensation between the corresponding aldehyde and 2,4-pentanedione. To

β-Cyclodextrin- and adamantyl-substituted poly(acrylate) self-assembling aqueous networks designed for controlled complexation and release of small molecules

• Liang Yan,
• Duc-Truc Pham,
• Philip Clements,
• Stephen F. Lincoln,
• Jie Wang,
• Xuhong Guo and
• Christopher J. Easton

Beilstein J. Org. Chem. 2017, 13, 1879–1892, doi:10.3762/bjoc.13.183

• , fluconazole [40] and curcumin [37], along with larger species exemplified by RNA and DNA segments [26][32][33][36][39][47]. Some systems are designed to target specific tissues [26][35]. We are particularly interested in the extent to which small molecule guest complexation and release characteristics may be

Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners

• Mohamed Ramadan El Sayed Aly,
• Hosam Ali Saad and
• Shams Hashim Abdel-Hafez

Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208

• bioavailability of anticancer drugs. Thus, SuberAniloHydroxamic acid–cholesterol conjugates (SAHA–cholesterol) [11], cholesterol-based charged liposomes encaging doxorubicin [12] or curcumin [13] showed higher activity compared with the native drugs. Synthetic coumarin-caged cholesterol derivatives, for instance

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• chemical means. The synthesized products can find a wide range of applications such as drug/gene delivery systems, flame retardant materials, conducting polymers, controlled release systems, diagnostic agents, and polymeric electrolytes for nano-crystalline solar cells. Curcumin (37) was converted to a

• diester using ethyl α-bromoacetate. The formed diester was copolymerized with PEG using CAL-B (Figure 14). The final product was an effective activator of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) several times better than the free curcumin [66]. The curcumin diester was used in a second polymer

• synthesis with carbinol (hydroxy) terminated polydimethylsiloxane catalyzed by CAL-B [67]. The curcumin moiety retained its fluorescence properties without quenching in thin films prepared from the polymer. Films exposed to low concentrations of vapors of the explosives DNT and TNT absorbed the explosives

Antioxidant potential of curcumin-related compounds studied by chemiluminescence kinetics, chain-breaking efficiencies, scavenging activity (ORAC) and DFT calculations

• Adriana K. Slavova-Kazakova,
• Silvia E. Angelova,
• Timur L. Veprintsev,
• Petko Denev,
• Davide Fabbri,
• Maria Antonietta Dettori,
• Maria Kratchanova,
• Vladimir V. Naumov,
• Aleksei V. Trofimov,
• Rostislav F. Vasil’ev,
• Giovanna Delogu and
• Vessela D. Kancheva

Beilstein J. Org. Chem. 2015, 11, 1398–1411, doi:10.3762/bjoc.11.151

• Physics and Technology, 9 Institutskiy per., Dolgoprudny, Moscow Region, 141700, Russian Federation 10.3762/bjoc.11.151 Abstract This study compares the ability to scavenge different peroxyl radicals and to act as chain-breaking antioxidants of monomers related to curcumin (1): dehydrozingerone (2

• activity for monomers and dimers with α,β-unsaturated side chains. Curcumin and 6 in fact are dimers of the same monomer 2. We conclude that the type of linkage between the two “halves” by which the molecule is made up does not exert influence on the antioxidant efficiency and reactivity of these two

• dimers. The dimers and the monomers demonstrated higher activity than Trolox (10) in aqueous medium (model 3). A comparison of the studied compounds with DL-α-tocopherol (11), Trolox and curcumin is made. All dimers are characterized through lower bond dissociation enthalpies (BDEs) than their monomers

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• , epigallocatechin-3-O-gallate, xanthohumol, (2S)-7,2’,4’-trihydroxy-5-methoxy-8-dimethylallylflavanone and genistein. Other compounds belong to the group of simple phenols (4-hydroxybenzyl alcohol), hydrolysable tannins (ellagic acid), stilbenoids (resveratrol) and diarylheptanoids (curcumin). In addition

• expression of vascular endothelial growth factor (VEGF) and matrix metalloproteinase (MMP)-9 decreased compared to the controls. No influence on the normal behavior of the animals was observed. In general, HBA represents an interesting anti-angiogenic agent for the treatment of angiogenic diseases. Curcumin

• Curcumin (3) is a natural product isolated from different Curcuma species (Zingiberaceae) some of which are used as raw material in the spice turmeric. It has been evaluated as a chemopreventive agent since the early nineties, and in 1998, Arbiser and co-workers [18] found that the compound also

SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

• Silke Felix,
• Louis P. Sandjo,
• Till Opatz and
• Gerhard Erkel

Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

• increase in caspase-3 activity (Figure 6D), indicating that the compound triggers the apoptotic cascade. Although several agents including natural products (e.g. curcumin, cucurbitacin, resveratrol) have been described to inhibit survivin expression by interfering with oncogenic signaling pathways [25][26

Functional properties of metallomesogens modulated by molecular and supramolecular exotic arrangements

• Alessandra Crispini,
• Mauro Ghedini and
• Daniela Pucci

Beilstein J. Org. Chem. 2009, 5, No. 54, doi:10.3762/bjoc.5.54

• -one) as a cyclometallating ligand and from the suitably functionalized curcumin β-diketonate as a complementary O,O chelating ligand (Figure 1). The presence of the principal ligand [39][40][41][42][43][44] introduces interesting luminescence properties into the metallic system (which is luminescent

• in solution), in the red region of the Vis spectrum (λ = 610 nm), with emission quantum yields in the range of 6–23%, depending on the solvent. However, the 3,4,5-trialkoxy-substituted benzoato fragment of the curcumin ligand imposes an overall hemi-disc structure to the resulting palladium

• from their synergy. Molecular structure of NIRPAC: a Pd(II) complex based on Nile red and a curcumin derivative. Molecular structure of Pd(II) complexes based on functionalised 2-phenylquinolines and β-diketonates. Some unusual palladiomesogens based on 3,5-disubstituted-2,2′-pyridylpyrroles and β