Benzophenone: a ubiquitous scaffold in medicinal chemistry

Surana, Khemchand R.; Chaudhary, Bharatkumar; Diwaker, Monika; Sharma, Satyasheel

doi:10.1039/c8md00300a

Cited by 76 publications

(59 citation statements)

References 108 publications

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“…Benzophenone is well known to react with UV light and generate radicals that can abstract hydrogen atoms from alkyl groups under ambient conditions, which is an efficient method of cross-linking bottlebrush homopolymers (41). The choice of benzophenone is also advantageous because its derivatives are well tolerated by the human body and found throughout medicinal chemistry (48) and personal care (49), suggesting that photocrosslinkers derived therefrom will not compromise the potential biocompatibility of 3D-printed bottlebrush elastomers. To demonstrate that formulations of PDMS-stat-PEO and PDMSbisBP can be 3D printed in analogy to the neat bottlebrush copolymers, Fig.…”

Section: Photocrosslinkable Formulationsmentioning

confidence: 99%

Room temperature 3D printing of super-soft and solvent-free elastomers

et al. 2020

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Super-soft elastomers derived from bottlebrush polymers show promise as advanced materials for biomimetic tissue and device applications, but current processing strategies are restricted to simple molding. Here, we introduce a design concept that enables the three-dimensional (3D) printing of super-soft and solvent-free bottlebrush elastomers at room temperature. The key advance is a class of inks comprising statistical bottlebrush polymers that self-assemble into well-ordered body-centered cubic sphere phases. These soft solids undergo sharp and reversible yielding at 20°C in response to shear with a yield stress that can be tuned by manipulating the length scale of microphase separation. The addition of a soluble photocrosslinker allows complete ultraviolet curing after extrusion to form super-soft elastomers with near-perfect recoverable elasticity well beyond the yield strain. These structure–property design rules create exciting opportunities to tailor the performance of 3D-printed elastomers in ways that are not possible with current materials and processes.

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Section: Photocrosslinkable Formulationsmentioning

confidence: 99%

Room temperature 3D printing of super-soft and solvent-free elastomers

et al. 2020

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“…Based on the statement that a chemical scaffold is defined as the structural core of a chemical compound [1], the concept of scaffold is a starting point in the design and development of new frameworks and gives a new lease of life to well-known structures. There is abundant literature [1][2][3][4][5][6][7][8][9][10][11][12] that presents various chemical frames and highlights the importance of this concept in different disciplines linked with drug discovery such as chemistry, pharmacy, and medicine. Considering a wide range of biological activities and a plethora of possible modifications, the stilbene is one of the most potent scaffolds in medicinal chemistry [2,13,14].…”

Section: Introductionmentioning

confidence: 99%

More Than Resveratrol: New Insights into Stilbene-Based Compounds

et al. 2020

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The concept of a scaffold concerns many aspects at different steps on the drug development path. In medicinal chemistry, the choice of relevant “drug-likeness” scaffold is a starting point for the design of the structure dedicated to specific molecular targets. For many years, the chemical uniqueness of the stilbene structure has inspired scientists from different fields such as chemistry, biology, pharmacy, and medicine. In this review, we present the outstanding potential of the stilbene-based derivatives. Naturally occurring stilbenes, together with powerful synthetic chemistry possibilities, may offer an excellent approach for discovering new structures and identifying their therapeutic targets. With the development of scientific tools, sophisticated equipment, and a better understanding of the disease pathogenesis at the molecular level, the stilbene scaffold has moved innovation in science. This paper mainly focuses on the stilbene-based compounds beyond resveratrol, which are particularly attractive due to their biological activity. Given the “fresh outlook” about different stilbene-based compounds starting from stilbenoids with particular regard to isorhapontigenin and methoxy- and hydroxyl- analogues, the update about the combretastatins, and the very often overlooked and underestimated benzanilide analogues, we present a new story about this remarkable structure.

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“…[1] Development of efficient methods for the C-C bond formation is one of the enduring research theme in organic chemistry. [2][3][4] Transition metal-catalyzed carbonylative Suzuki cross-coupling reaction is one of the powerful methods to generate C-C bonds which are an integral part of structural skeleton of a wide variety of natural products, pharmaceutical drugs, agrochemicals, fine chemicals, and organic functional materials [5][6][7][8][9][10] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate

Layek

Agrahari

Ganguly

et al. 2020

Applied Organom Chemis

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Benzoylhydrazone Schiff base–ligated three new ONO pincer–type palladium(II) complexes, [(PdL1(PPh3)] (1), [(PdL2(PPh3)] (2), and [(PdL3(PPh3)] (3), were synthesized by the reaction of the respective ligand, N‐(2‐hydroxybenzylidene)benzohydrazide (HL1), N‐(2‐hydroxy‐3‐methoxybenzylidene)benzohydrazide (HL2), or N‐(5‐bromo‐2‐hydroxybenzylidene) benzohydrazide (HL3), with Pd(OAc)2 and PPh3 in methanol and isolated as air‐stable reddish‐orange crystalline solids in high yields (78%–83%). All three complexes were fully characterized by elemental analysis, Fourier‐transform infrared spectroscopy, UV–Visible, 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, and 31P{1H} NMR spectroscopic studies. The molecular structure of all three complexes was established unambiguously by single‐crystal X‐ray diffraction studies which revealed a distorted square planar geometry of all three complexes. The ONO pincer–type ligands occupied three coordination sites at the palladium, while the fourth site is occupied by the monodentate triphenylphosphine ligand. The catalytic potential of all three complexes was explored in the carbonylative Suzuki coupling of aryl bromides and iodides with arylboronic acids to yield biaryl ketones, using CHCl3 as the source of carbonyl. The reported protocol is convenient and safe as it obviates the use of carbon monoxide (CO) balloons or pressured CO reactors which are otherwise needed for the carbonylation reactions. The methodology has been successfully applied to the synthesis of two antineoplastic drugs, namely, phenstatin and naphthylphenstatin, in good yields (81% and 85%, respectively). Under the optimized reaction conditions, complex 2 exhibited the best catalytic activity in the carbonylative Suzuki couplings. The reported catalysts have wide reaction scope with good functional group tolerance. All catalysts could be retrieved from the reaction after completion and recycled up to three times with insignificant loss in the catalytic activity.

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Benzophenone: a ubiquitous scaffold in medicinal chemistry

Abstract: Diaryl ketones are an important scaffold in drug discovery due to their prevalence in naturally occurring bioactive compounds. This review discusses molecules containing the benzophenone moiety that have potent biological activity.

Cited by 76 publications

References 108 publications

Room temperature 3D printing of super-soft and solvent-free elastomers

Room temperature 3D printing of super-soft and solvent-free elastomers

More Than Resveratrol: New Insights into Stilbene-Based Compounds

Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate

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