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Background: Peyronie's disease (PD) is a localized fibrosis of tunica albuginea, which causes the anatomical and functional changes to the penis. Corporoplasty with grafting is indicated in severe (>60°) and complex curvature. Buccal mucosa is the most favored autologous graft material nowadays. The ventrolateral aspect of lingual mucosa has similar histological features to the rest of the oral cavity. Methods: This study aimed to test the efficacy, safety, durability, and reproducibility of corporoplasty with lingual mucosal graft (LMG) in the surgical treatment of PD in terms of surgical outcome, sexual function, and donor site complications. This prospective study included 19 patients of PD with severe and complex curvature, who underwent corporoplasty with LMG. Surgical and functional outcomes were assessed at follow-up planned at 2 weeks, 3 months, 6 months, 1 year, and 2 years. Results: The mean operative time was 126.31 ± 21.45 min. Additional Nesbit's plication to correct the residual deformity was required in 26% (5 / 19) of patients. Straightening of the penis (curvature <10°) was achieved in 89% (17 / 19) of patients. Increase in the penile length (>1 cm) postoperatively was achieved in 63% (12 / 19) of patients and a shortening of penis occurred in 5% (1 / 19) of patients. Newer onset erectile dysfunction developed in 11% (2 / 19) of patients, and patient and partner satisfaction rates were 89% (17 / 19) and 84% (16 / 19), respectively, in a mean follow-up of 20.66 ± 5.37 months. Donor site complications were minimal and no patient had any salivary changes or speech disturbances. Conclusion: LMG provided excellent short-term results in terms of deformity correction, improved sexual function, and minimal donor site morbidity. The method is simple and reproducible, and multicenter studies with larger number of cases with longer follow-up are required to confirm these favorable results. [ABSTRACT FROM AUTHOR]

Tyrosinase is a copper‐containing enzyme involved in the biosynthesis of melanin pigment. While the excess production of melanin causes hyperpigmentation of human skin, hypopigmentation results in medical conditions like vitiligo. Tyrosinase inhibitors could be used as efficient skin whitening agents and tyrosinase agonists could be used for enhanced melanin synthesis and skin protection from UV exposure. Among a wide range of tyrosinase‐regulating compounds, natural and synthetic derivatives of furochromenones, such as 8‐methoxypsoralen (8‐MOP), are known to both activate and inhibit tyrosinase. We recently reported a synthetic approach to generate a variety of dihydrofuro[3,2‐c]chromenones and furo[3,2‐c]chromenones in a metal‐free condition. In the present study, we investigated these compounds for their potential as antagonists or agonists of tyrosinase. Using fungal tyrosinase‐based in vitro biochemical assay, we obtained one compound (3k) which could inhibit tyrosinase activity, and the other compound (4f) that stimulated tyrosinase activity. The kinetic studies revealed that compound 3k caused 'mixed' type tyrosinase inhibition and 4f stimulated the catalytic efficiency. Studying the mechanisms of these compounds may provide a basis for the development of new effective tyrosinase inhibitors or activators. [ABSTRACT FROM AUTHOR]

Herein, DFT studies corroborating experimental results revealed that the shortest intramolecular hydrogen bonding distance of cis/trans‐oxaphosphetane (OPA) oxygen with the CH‐hydrogen of a triphenylphosphine phenyl ring provides good evidence for the attained olefin Z/E‐selectivity in Wittig olefination of the studied examples. 2‐Nitrobenzaldehyde, 3‐nitrobenzaldehyde, 2‐nitro‐3‐bromobenzaldehyde, 2‐nitro‐5‐bromobenzaldehyde and 2‐nitro‐5‐arylbenzaldehydes provided Z‐nitrostilbenes with (2‐chloro‐4‐hydroxy‐3‐methoxy‐5‐(methoxycarbonyl)benzyl) triphenylphosphonium chloride as the major products. However, 4‐nitrobenzaldehyde and 2‐nitro‐6‐bromobenzaldehydes furnished E‐nitrostilbenes as the major products in high yields. Furthermore, the DFT computed intramolecular CH1/CH2‐hydrogen bond distances with Cl/NO2 of selected stilbene derivatives were in good agreement with intramolecular hydrogen bond distances measured from single‐crystal X‐ray diffraction measurements. [ABSTRACT FROM AUTHOR]

A facile one-step synthetic approach to dihydrofuro-[3,2- c ]chromenones and furo[3,2- c ]chromenones by the reaction of methyl enol ethers with 4-hydroxycoumarins under metal-free conditions is presented. Dihydrofuro[3,2- c ]chromenones and furo[3,2- c ]-chromenones were selectively obtained by controlling the stoichiometry of boron trifluoride diethyl etherate. An unexpected aryl-group migration followed by aromatization of the furan moiety, leading to a variety of furo[3,2- c ]chromenone derivatives in good yields, is reported. [ABSTRACT FROM AUTHOR]

The first total synthesis of acylphloroglucinol-based natural products faberiones A, B, and E is reported, which were isolated from Hypericum faberi. Total syntheses of faberiones A and B are accomplished in six linear steps from commercially accessible 1,3,5-trimethoxybenzene (methyl protected form of phloroglucinol) in overall yields of 31 and 33% respectively, via simple and straightforward approaches that include acylation, o-methoxy deprotection, selective iodination and tandem-Sonogashira cyclization followed by C-geranylation. Faberione E is achieved in two linear steps from acylphloroglucinol with an overall yield of 57% via geranylation followed by benzopyran formation reaction. [ABSTRACT FROM AUTHOR]

An efficient approach for synthesizing fused nitrogen containing heterocycles has been formulated. The approach relies on the use of 2-bromo-3-(arylamino)-1H-inden-1-one derivatives as precursors for the synthesis of indenoindoles and indenoisoquoinolines. The synthesis of indenoindoles is achieved via palladium-catalyzed C-H activation strategy, while a sequential palladium-catalyzed intermolecular Suzuki coupling followed by an intramolecular annulation process is used to synthesize indenoisoquinolines. The developed strategy offers indenone fused polycycles in moderate to good yields. [ABSTRACT FROM AUTHOR]

A mild and transition‐metal‐free one‐pot strategy is established to prepare polysubstituted naphthalene and phenanthrene derivatives from methyl enol ethers (MEE) with alkynes. Significantly, this protocol is promoted by boron trifluoride diethyl etherate (BF3⋅Et2O) at room temperature. A wide variety of diversely functionalized naphthalene and phenanthrene derivatives were obtained in good to excellent yields. A plausible mechanism involving a spiro quinonoid intermediate is proposed. Due to fluorescent nature of naphthalene, selected compounds were screened for the solvatochromism study. Notably, positive solvatochromism effect was observed in the case of nitro‐substituted naphthalene derivative (3 h) with respect to different polarity of solvents. [ABSTRACT FROM AUTHOR]

Background: Xanthogranulomatous pyelonephritis (XGP) is chronic pyelonephritis subtype where in renal parenchymal destruction occurs and therefore results in progressive loss of kidney functions. Although middle age group is the predominant age group affected but it can be seen at any age. There is accumulation of macrophages (lipid-laden) leading to renal parenchymal destruction and fibrosis. In this study, we present our data of 15 patients who had undergone nephrectomy and were biopsy proven XGP. Aims and Objectives: The aim of the study was to describe the clinical and radiological features of XGP in adults. Materials and Methods: XGP constituted 4.31% of the 348 nephrectomies done for infective causes over a period of 7 years. All our patients had undergone unilateral total nephrectomy. Demographic and clinical records were analyzed after consent from all the patients. Results: The age range in our study was 18–65 years with mean 42.93±15.66 years. Nine of our patients, that is, 60% were females. Diabetes was present in 53.3% of our patients. Three patients had imaging suggestive of pyonephrosis, three patients had perinephric collection and 9 patients (60%) had concomitant nephrolithiasis. All the kidneys were grossly enlarged and were non-functional on renal scintigraphy. Conclusion: XGP is a form of chronic pyelonephritis which although being less common but is devastating given the destruction of renal parenchyma it does and associated morbidity. Clinicoradiologic correlation cannot be overemphasized. The definitive diagnosis is established after histopathologic examination. [ABSTRACT FROM AUTHOR]

A stereoselective strategy for the replacement of the 1,2-dihaloalkene bridge of tetrahalonorbornyl derivatives by an oxygen bridge involving stepwise controlled oxidation, cleavage of the dione thus formed, and reiterative intramolecular S(sub N)2 displacement of two bridgehead halogens is devised. The synthesis of four highly strained pentacyclic bis-oxa-bridged derivatives with interesting structural variations is presented.

[Display omitted] A simple yet efficient approach towards the synthesis of β -hydroxy selanylated ketones was developed from easily accessible chalcones and diphenyl diselenide through an electrochemical pathway. In this technique, diphenyl diselenide and water are the source of PhSe. and hydroxyl (–OH) groups that can be inserted at the α and β positions respectively producing β -hydroxy selanylated ketones in moderate to good yields. The reaction features difunctionalization of ketones, catalyst free, mild reaction conditions, stereo and regioselectivity in an undivided electrochemical cell at room temperature. For this transformation, a plausible radical mechanism has been put out. [ABSTRACT FROM AUTHOR]

A tandem, one-pot reaction of 2,3-dibromoindenone with phenols is reported, which provides a straightforward approach to accomplish structurally diverse indenobenzofurans in excellent yields. Besides, the control experiments revealed that reaction proceeds through a two-step sequence via an intermolecular Michael addition-elimination reaction, which enables the C-O bond formation, followed by palladiumcatalyzed intramolecular C-C bond formation through C-H activation. Significantly, this protocol offers a convenient approach to synthesize the diverse tetracyclic indenobenzofurans. [ABSTRACT FROM AUTHOR]

Research has been conducted on the gamma-lactone-fused cyclopentanoids. The effect of the tetrahalonorborene derivatives' structural flexibility and stereochemical control on these cyclopentannulated gamma-lactones has been investigated and the details are described.

The role of pi-allylpalladium intermediate in the organic synthesis is central to the palladium-catalyzed reactions of allenes with carbon and heteroatom nucleophiles. The application and reactivity of the pi-allylpalladium species in the synthesis of natural products using allenes and mechanistic aspects of reactions involved are discussed.

Alkyl enol ethers (AEE) are versatile synthetic intermediates with a unique reactivity pattern. This review article summarizes the synthesis of AEE as well as its reactivity and how enol ether undergoes intermolecular reactions for various bond formation, leading to the construction of several useful organic molecules. The synthetic applications of alkyl enol ethers towards intermolecular bond‐forming reactions include metal‐catalyzed reactions, cycloaddition and heterocycle formation as well as rwactions in the field of natural products synthesis. The achievement of these impressive transformations prove the countless synthetic potential of AEE. The main objective of this review is to bring attentiveness among synthetic chemists to show how AEE extensively can be used to react with both electrophiles as well as nucleophiles, thereby behaving as an ambiphilic reactant. We trust that the unique reactivity pattern of alkyl enol ethers and the fundamental mechanistic idea can attract chemists in AEE chemistry. Exclusively, intermolecular reactions of AEE with other functionalized moieties have not been reviewed to the best of our knowledge. [ABSTRACT FROM AUTHOR]

A simple computational model explains and predicts pi-facial selectivity in nucleophilic additions to sterically-free carbonyls. The model, based on MNDO, uses two sets of calculations. One measures electrostatic and polarization effects using a test charge to represent the nucleophile, while the other models the hydride ion to determine the added role of orbital interactions. Using these two, the approach is able to reproduce most empirically-established selectivities, especially with the hydride model.

Stereoselective formal synthesis of (_)-neplanocin A from a cyclopentane derivative is described by using an elegant strategy involving reiterative usage of an already existing acetonide protecting group. The acetonide protecting groups that is carried forward intact right from the starting adduct to an advanced intermediate is shuffled around twice as in a relay race through the synthetic sequence, which has avoided unnecessary employment of additional protecting groups.

A full account of the total synthesis of (±)-cassumunins A–C – superior antioxidants and anti-inflammatory agents – is given. Two novel approaches were developed for synthesizing cassumunins. The total synthesis of cassumunins A and B was accomplished in five linear steps from a known aldehyde in good overall yields of 50 and 43%, respectively, featuring a cascade [3,3]-sigmatropic shift (the Claisen rearrangement) and Heck cross-coupling reaction. Consequently, the total synthesis of cassumunin C was accomplished in three linear steps from a known alcohol with an overall yield of 53%. The key features involved in this synthesis are tandem [3,3]-sigmatropic shift, SN 2′ reaction, and aldol condensation. Moreover, a total of eighteen symmetrical and unsymmetrical curcumin analogues were synthesized. [ABSTRACT FROM AUTHOR]

The first total synthesis of enisorine D, a natural product isolated from the marine sponge Iotrochota cf. iota , is described in 64% overall yield. The target molecule, which is an inhibitor of T3SS-dependent Yope secretion of Y. pseudotuberculosis , is achieved in seven linear steps from tyramine via simple and effective transformations that include bromination, acylation, alkylation, azidation, reduction and routine acid–amine coupling. A total of sixteen analogues are prepared by coupling with eight different cinnamic acids, two bromopyrrole carboxylic acids, five phenyl carboxylic acids and picolinic acid. [ABSTRACT FROM AUTHOR]

A study aimed to achieve a short and stereoselective route to the trans-hydrindane derivative, which is a potential building block for the synthesis of steroidal and related molecules. The desired results were obtained by the operation of indium, tin, and ruthenium based reagents, starting from a tetrabromo norbornyl derivative.

Research has been conducted on 7-azaspiro[4.5]decan-6-ones. The authors describe the access to these compounds which involves regio- and chemoselective reactions and starts from tetrabromonorbornyl derivatives.

Abstract 1,6-Conjugate addition of various carbon nucleophiles to p -quinone methide surrogate is reported. The active methylene containing C -nucleophiles such as 1,3-diketones, diesters and ketoesters underwent two consecutive additions leading to bis-addition products, diarylpropanes. Whereas, nitroalkanes proceeded to contribute mono-addition products. Surprisingly, bromo analogue of p -quinone methide surrogate underwent halophilic dimerization reaction with excellent yield. The reported strategy provides an efficient synthesis of 1,3-diarylpropane derivatives bearing pharmacophoric ortho -methoxy phenol moiety under mild reaction conditions. Graphical abstract Image 1 Highlights • Two consecutive 1,6-conjugate additions of carbon nucleophiles to p -quinone methide surrogate is reported. • This strategy was found amenable to 1,3-ketoesters, diesters, diketones and nitroalkane compounds. • Wide substrate scope and good to excellent yields are reported under mild reaction conditions. • It is a novel strategy for the synthesis of 1,3-diarylpropanes bearing pharmacophoric ortho -methoxy phenol moiety. • Formation of an unexpected dimerized product through a halophilic reaction is reported. [ABSTRACT FROM AUTHOR]

We herein report a serendipitously observed acid mediated rearrangement of monoethylene ketal of 2-methyl-2-(3-methylbut-2-en-1-yl)cyclohex-4-ene-1,3-diones to Dihydrobenzopyran and demonstrated the application of this methodology in the construction of core carbon scaffolds of dimethoxyajacareubin, cariphenone-A and crotamadine. [ABSTRACT FROM AUTHOR]

The expeditious route for the synthesis of γ-butyrolactone fused cyclooctene starting from the γ-butyrolactone fused cyclopentane through bicyclo[4.2.1]nonan-9-one is reported. Retro-Dieckmann's condensation of bicyclo[4.2.1]nonan-9-one in presence of sodium methoxide and methanol furnished γ-butyrolactone fused cyclooctene in good yield. Surprisingly, the stereochemistry of ringjunction of γ-butyrolactone fused cyclooctene is different from the γ-butyrolactone fused cyclopentane, and the position of new ester group, which were confirmed unambiguously by X-ray analysis. [ABSTRACT FROM AUTHOR]

An elegant application wherein a one-pot synthesis of a highly oxygenated strained bis-oxa-bridged compound is delineated from the bis-alpha-diketone and generalized to other substrates is reported. A simple and efficient procedure for the conversion of a 2:1 Diels-Alder adduct between tetrachloro-5,5-dimethoxyclopentadiene and 1,4-cyclohexadiene into a highly symmetric pentacyclic bis-oxa-bridged compounds.

Research is presented concerning the creation of alpha-diketones from vicinal dihaloakenes through a facile conversion process. The production of symmetric, polycyclic bis(alpha-diketone) is discussed.

The formation of a twist-brendane via intramolecular enolate alkylation is described. Conversion of bicyclo[2.2.1]heptane scaffold present in this twist-brendane through a Grob-type fragmentation to unravel a functionalized bicyclo[2.2.2] system which contains all the necessary carbon atoms of the lipophilic core structure of nor-platencin, a platencin analogue is presented. Synthesis of core structure of platencin was also accomplished by extending this strategy to a starting material possessing a surrogate for the exocyclic methylene group. [ABSTRACT FROM AUTHOR]

A selective debromination of tetracyclic dibrominated bis-γ- lactones in the presence of triethylamine and mesyl chloride is reported. Both mesyl chloride and triethylamine are essential for the debromination process. The reduction is proposed to proceed through halophilic substitution of electrophilic bromine. The source of the halophile in this reaction is believed to be triethyl(mesyl)ammonium chloride. The nonoccurrence of debromination in dibromo bis-γ-lactones with tosyl chloride and triethylamine as reagents suggests that the formation of a source of well-dissociated chloride ions during the reaction is necessary. Furthermore, selective debromination of dibrominated bis-γ-lactones was also achieved by using pyridine-thionyl chloride as a reagent. Alternatively, potassium chloride-[18-crown-6] was demonstrated to be a suitable source of chloride ion for the reduction of bromolactones. [ABSTRACT FROM AUTHOR]

A facile and efficient base promoted one-pot dimerization of halo cyclohexene derivatives leading to a de novo synthesis of biologically important diarylmethane and diarylmethanone derivatives is reported. A plausible mechanism for the unexpected formation of the title compounds involves dehydrohalogenation, 1,6-conjugate addition, subsequent aromatization through C–C bond cleavage and dehydrohalogenation. [ABSTRACT FROM AUTHOR]

The base-mediated formation of a bridgehead double bond in a bicyclo[2.2.1]heptane system (anit-Bredt molecules) is described. The synthesis of exocyclic norbornyl enones by Wittig reaction of α-diketones is reported. These enones and their Michael adducts are used as substrates for the generation of transient bridgehead enones and their trapping with MeOH and H2O. Bridgehead alcohols are easily synthesized from norbornyl enones and are exploited for the diversity oriented synthesis of frameworks of natural and unnatural products. [ABSTRACT FROM AUTHOR]

A diastereoselective zinc-mediated propargylation of non-enolizable norbornyl α-diketones and an efficient AgI-catalyzed cycloisomerization of the resulting α-keto homopropargyl alcohols with terminal alkynes leading to spirocyclic dihydrofurans have been reported. The dihydrofurans obtained were subjected to hydrogenation to afford spiro tetrahydrofuran derivatives in nearly quantitative yields (98-99 %). Eventually, the prepared α-spiro tetrahydrofuran norbornyl monoketones were utilized as precursors for acid-mediated Grob-type fragmentation reactions and converted into 1-oxaspiro[4.5]decan-6-one derivatives by treatment with p-toluenesulfonic acid. [ABSTRACT FROM AUTHOR]

A macrocyclic furanobutenolide was crafted from readily available furan building-blocks to set-up a transannular Diels–Alder reaction which delivered the carbocyclic core present in a class of cembranoid diterpene natural products. [ABSTRACT FROM AUTHOR]

Total syntheses of two antimicrobial natural products (±)-cis-neocnidilide and (±)-trans-neocnidilide starting from a readily preparable cyclohexa[b]-fused 5-oxabicyclo[2.1.1]hexane derivative are presented. The diastereomeric tetrahydrofuran tricarboxylate epimers obtained from a BF3⋅OEt2 promoted Grob-type fragmentation of the oxa-bicycle derivative were converted into title natural products by employing pyridinium dichromate/acetic anhydride mediated bis-oxidative cleavage reaction. [ABSTRACT FROM AUTHOR]