bluuebunny/crossref_metadata_2025_split huggingface dataset:
ChemInform Abstract: Efficient Access to Naphthoquinon‐1,3‐dithioles: Formal Cycloaddition and Oxidation of Quinones and Amines with CS2.
Authors: Huang Huan‐ming , Li Yu‐jin , Yang Jian‐rong , Jia Jian‐hong , Ye Qing , Han Liang , Gao Jian‐rong 
Published: October 2013

AbstractA simple synthetic access to naphthoquinon‐1,3‐dithiole derivatives proceeds through a formal cycloaddition and oxidation reaction of 1,4‐naphthoquinone derivatives and amines in the presence of CS2 without an additional oxidant.
ChemInform Abstract: Enantioselective 1,3‐Dipolar Cycloaddition of Methyleneindolinones and N,N′‐Cyclic Azomethine Imines
Authors: Hong Liang , Kai Ming , Wu Chongyang , Sun Wangsheng , Zhu Gongming , Li Guofeng , Yao Xiaojun , Wang Rui 
Published: October 2013

Abstractleading to spiro‐pyrazolidin‐3,3′‐oxindoles (III) in good to high yields
ChemInform Abstract: Synthesis and Antibacterial Activity of 4‐Aryl‐2‐(1‐substituted ethylidene)thiazoles.
Authors: Hassan Alaa A. , Ibrahim Yusria R. , El‐Sheref Essmat M. , Abdel‐Aziz Mohamed , Braese Stefan , Nieger Martin 
Published: October 2013

Abstract9 Title compounds of type (III) and 9 of type (V) are prepared; 9 of them are screened for their in vitro antibacterial activities.
ChemInform Abstract: Reactions of Dimethyl Ethynedicarboxylate with (Substituted ethylidene)hydrazinecarbothioamides.
Authors: Hassan Alaa A. , Ibrahim Yusria R. , Aly Ashraf A. , El‐Sheref Essmat M. , Yamato Takehiko 
Published: October 2013

AbstractAlternative product structures are ruled out on the basis of spectroscopic data which are consistent only with the described thiazolidin‐4‐ones.
ChemInform Abstract: Unsymmetrical Benzotristhiazole: A New Electron‐Withdrawing Core for Octupolar Chromophores.
Authors: Fueloepova Andrea , Magdolen Peter , Karolyiova Miroslava , Sigmundova Ivica , Zahradnik Pavol 
Published: October 2013

AbstractNovel benzimidazoles (II) and (IV) as well as the new unsymmetrical benzotristhiazoles (VI) and (VIII) are synthesized.
ChemInform Abstract: Microwave‐Assisted Synthesis and Biological Evaluation of Some Benzimidazole Derivatives Containing a 1,2,4‐Triazole Ring.
Authors: Mentese Emre , Karaali Nesrin , Yilmaz Fatih , Uelker Serdar , Kahveci Bahittin 
Published: October 2013

AbstractA series of title compounds are prepared and screened for their lipase inhibition and antioxidant activities.
ChemInform Abstract: Catalytic Activity of Dithioic Acid Copper Complexes in the Alkyne—Azide Cycloaddition.
Authors: Velasco Bayardo E. , Lopez‐Tellez Gustavo , Gonzalez‐Rivas Nelly , Garcia‐Orozco Ivan , Cuevas‐‐Yanez Erick 
Published: October 2013

AbstractA dithioic acid copper complex derived from acetophenone exhibits excellent catalytic activity in the synthesis of a variety of triazole derivatives (III) (39 examples) via alkyne—azide cycloaddition reactions.
ChemInform Abstract: Synthesis and Antioxidant Activities of Acetamidomethylsulfonyl Bis Heterocycles‐oxazolyl/thiazolyl/imidazolyl‐1,3,4‐oxadiazoles.
Authors: Basha Nabhubygari Mahaboob , Lavanya Gopala , Padmaja Adivireddy , Padmavathi Venkatapuram 
Published: October 2013

Abstract9 Title compounds of type (IX) are prepared and screened for their anti‐oxidant activities.
ChemInform Abstract: Synthesis and Antimicrobial Activity of New Tetrazoles Incorporating Isoindole‐1,3‐dione Moiety and Their Sugar Derivatives.
Authors: Abdel‐Rahman Adel A.‐H. , Ali Omar M. , Abdel‐Megeed Amira A.‐S. 
Published: October 2013

AbstractNovel sugar substituted heterocycles like (I) and (II) are synthesized and tested for their antimicrobial activity.
ChemInform Abstract: 5‐Hydroxypent‐2‐enenitriles as Precursors Toward Dihydropyranones, Dienenitriles and Functionalized Naphthalenes.
Authors: Zhang Xinying , Jia Xuefei , Liu Nan , Guo Xiaojie , Song Yunping , Fan Xuesen 
Published: October 2013

AbstractThe treatment of a variety of 4‐hydroxypent‐2‐enenitriles with sulfuric acid at elevated temperature is described.
ChemInform Abstract: Silicon‐Mediated Highly Efficient Synthesis of 1,8‐Dioxo‐octahydroxanthenes and Their Transformation to Novel Functionalized Pyrano‐tetrazolo[1,5‐a]azepine Derivatives.
Authors: Soliman Hanan A. , Salama Tarek A. 
Published: October 2013

AbstractTitle compounds (III) are prepared in high yields via a cascade Knoevenagel—Michael condensation followed by cyclodehydration utilizing SiCl4 as catalyst.
ChemInform Abstract: Methods for the Synthesis of Chiral Sulfur Heterocycles and Their Application in the Asymmetric Baylis—Hillman Reactions.
Authors: Periasamy Mariappan , Gurubrahamam Ramani , Muthukumaragopal Gopal P. 
Published: October 2013

AbstractDimesylates of chiral diols cyclize in the presence of sodium sulfide to provide sulfur heterocycles (III) and (VII).
ChemInform Abstract: Gold‐Catalyzed Intramolecular Regio‐ and Enantioselective Cycloisomerization of 1,1‐Bis(indolyl)‐5‐alkynes.
Authors: Huang Long , Yang Hai‐Bin , Zhang Di‐Han , Zhang Zhen , Tang Xiang‐Ying , Xu Qin , Shi Min 
Published: October 2013

AbstractA novel Au(I)‐catalyzed 6‐endo‐dig cyclization of 1,1‐bis(indolyl)‐5‐alkynes (I) and (III) is developed to give bis(indole) alkaloid analogues through a pseudo 1,5‐migration of an indole moiety.
ChemInform Abstract: The Synthesis and Antibacterial Activity of Novel 4‐Pyrrolidin‐3‐cyanopyridine Derivatives.
Authors: Bogdanowicz Agnieszka , Foks Henryk , Gobis Katarzyna , Kedzia Anna , Kwapisz Ewa , Olczak Andrzej , Glowka Marek L. 
Published: October 2013

AbstractThe unexpectedly obtained butadiene derivative (III) is cyclized to main intermediate (IV) which is suitable for classical nucleophilic aromatic substitution reactions at the halogen (not shown).
ChemInform Abstract: Regioselective lateral or Vinyl C—H Lithiation/1,5‐Retro‐Brook Rearrangement via Quinolyl or Pyridyl Ring Directed Deprotonation.
Authors: He Yongping , Ma Bin , Yang Juan , Xie Xingang , She Xuegong 
Published: October 2013

AbstractTreatment of arylsiloxanes of type (I) with excess amounts of LDA in refluxing THF results in quinolyl directed lateral C‐H lithiation/1.5‐retro‐Brook rearrangement to give C‐silylated derivatives (II) regioselectively.
ChemInform Abstract: Synthesis of 1‐Substituted Tetrahydroisoquinolines by Lithiation and Electrophilic Quenching Guided by in situ IR and NMR Spectroscopy and Application to the Synthesis of Salsolidine, Carnegine and Laudanosine.
Authors: Li Xiabing , Leonori Daniele , Sheikh Nadeem S. , Coldham Iain 
Published: October 2013

AbstractThe simple base BuLi is able to deprotonate tetrahydroisoquinolines at low temperature in less than 5 minutes.
ChemInform Abstract: One‐Pot Synthesis of Pyrrolo[1,2‐a]quinolin‐1‐ones by the Cyclocondensation of 5‐Hydroxy‐1‐arylpyrrolidin‐2‐ones with Dicarbonyls.
Authors: Wang Xuerui , Zhang Wenxue , Shen Hongjuan , Zhang Wei 
Published: October 2013

AbstractThe transformation proceeds as a two‐step process consisting of an initiatory acid‐catalyzed coupling reaction between N‐acyliminium ions and 1,3‐dicarbonyls followed by a phosphorus pentoxide or sulfuric acid‐promoted intramolecular Friedel‐Crafts acylation.
ChemInform Abstract: Synthesis of Novel Fluorinated 11H‐Azaindolo[3,2‐c]isoquinolines.
Authors: Atmakur Krishnaiah , Emmadi Narender Reddy , Balasubramanian Sridhar 
Published: October 2013

AbstractAttempts to cyclize pyrrolo[2,3‐b]pyridins (II) via Pictet‐Spengler reaction failed.
ChemInform Abstract: Copper‐Catalyzed Synthesis of Imidazol[1,2‐α]pyridines Through Tandem Imine Formation‐Oxidative Cyclization under Ambient Air: One‐Step Synthesis of Zolimidine on a Gram‐Scale.
Authors: Bagdi Avik Kumar , Rahman Matiur , Santra Sougata , Majee Adinath , Hajra Alakananda 
Published: October 2013

AbstractThe simple cyclization reaction of 2‐aminopyridines and ketones is tolerant to a wide range of functional groups.
ChemInform Abstract: Facile Construction of 1,2,6,7,12,12b‐Hexahydroindolo[2,3‐a]quinolizines via One‐Pot Three‐Component Reactions of Tryptamines, Propiolate, and α,β‐Unsaturated Aromatic Aldehydes or Ketones.
Authors: Sun Jing , Zhang Li‐Li , Yan Chao‐Guo 
Published: October 2013

AbstractThe title one‐pot two‐step process proceeds efficiently with ZnCl2 as promoter for the cyclization step.
ChemInform Abstract: One‐Pot Synthesis of Quinazoline Derivatives via [2 + 2 + 2] Cascade Annulation of Diaryliodonium Salts and Two Nitriles.
Authors: Su Xiang , Chen Chao , Wang Yong , Chen Junjie , Lou Zhenbang , Li Ming 
Published: October 2013

AbstractA series of 2,4‐disubstituted quinazolines (III), (VI), and (X) is prepared by [2 + 2 + 2] cascade annulation of diaryliodonium salts with excess of nitriles.
ChemInform Abstract: Synthesis of Novel Pyrimido[4,5‐b]quinolin‐4‐ones with Potential Antitumor Activity.
Authors: Insuasty Braulio , Becerra Diana , Quiroga Jairo , Abonia Rodrigo , Nogueras Manuel , Cobo Justo 
Published: October 2013

AbstractThe novel heterocycles (III) and (V) as well as their corresponding chloranil oxidation products (not shown) are evaluated against a panel of cancer cell lines.
ChemInform Abstract: Reactivity of 7‐Amino‐3‐tert‐butyl‐4‐oxo‐4,6‐dihydropyrazolo[5,1‐c] [1,2,4]triazine‐8‐carbonitrile.
Authors: Mironovich L. M. , Kostina M. V. , Podol'nikova A. Yu. 
Published: October 2013

AbstractTitle compounds (III), (V) and (VII) possess antimicrobial activities.
ChemInform Abstract: Phosphane‐Catalyzed [3 + 2] Cycloaddition Reaction of Allenoate and Cyclic Imines: A Simple and Efficient Method for Synthesis of Benzo‐Fused Cyclic Sulfamidate Heterocycles.
Authors: Wang You‐Qing , Zhang Yongna , Dong Haina , Zhang Jie , Zhao Jin 
Published: October 2013

AbstractTriphenylphosphane is used as an organocatalyst for the synthesis of the title compounds.
ChemInform Abstract: A New Synthetic Approach for Functional Triisopropoxyorganosilanes Using Molecular Building Blocks.
Authors: Maegawa Yoshifumi , Waki Minoru , Umemoto Akinari , Shimada Toyoshi , Inagaki Shinji 
Published: October 2013

AbstractThe novel synthetic route for the synthesis of building blocks containing triisopropyloxysilyl groups is based on the sequential reaction of substrates (I) with trichlorosilane and 2‐propanol.
ChemInform Abstract: Novel Amino Acids: Synthesis of Furoxan and Sydnonimine Containing Amino Acids and Peptides as Potential Nitric Oxide Releasing Motifs.
Authors: Nortcliffe Andrew , Botting Nigel P. , O'Hagan David 
Published: October 2013

AbstractThe synthesis of four novel amino acids carrying nitric oxide‐releasing motifs is presented (protected derivatives (VI), (VIII), and (X) are depicted).
ChemInform Abstract: Enantioselective Synthesis of (+)‐(S)‐7,8‐Dihydrokavain and (4R,6R)‐4‐Hydroxy‐6‐(2‐phenylethyl)tetrahydro‐2H‐pyran‐2‐one, Lactone Analogue of Compactin and Mevinolin.
Authors: Mineeva I. V. 
Published: October 2013

AbstractSimple and efficient synthesis of (+)‐(S)‐7,8‐dihydrokavain (I) and (4R,6R)‐4‐hydroxy‐6‐(2‐phenylethyl)tetrahydro‐2H‐pyran‐2‐one (II) is performed, involving Keck allylation and Binol as catalyst in the key stage of building up the carbon scaffold of the target molecule.
ChemInform Abstract: Synthesis and Antitumor Activity of Novel 4‐(2‐Fluorophenoxy)quinoline Derivatives Bearing the 4‐Oxo‐1,4‐dihydroquinoline‐3‐carboxamide Moiety.
Authors: Li Sai , Jiang Rui , Qin Mingze , Liu Haicheng , Zhang Guangyan , Gong Ping 
Published: October 2013

Abstract19 Title compounds with the skeleton of (X) carrying a variety of substituents and cyclic amine components are prepared and tested for their antitumor activities.
ChemInform Abstract: Growth, Crystal Structure and Spectrum of a Novel Rare‐Earth Orthophosphate Crystal: Yb:LuPO4.
Authors: Zhong De‐gao , Teng Bing , Cao Li‐feng , Chao Wang , He Lin‐xiang , Li Jian‐hong , Zhang Shi‐ming , Li Yu‐yi 
Published: October 2013

AbstractLuPO4:Yb crystals of 6 x 2 x 0.5 mm maximum size are grown from Yb2O3 and Lu2O3 in a Pb2P2O7 flux as high‐temperature solvent.
ChemInform Abstract: Metal—Organic‐Frameworks‐Derived General Formation of Hollow Structures with High Complexity.
Authors: Zhang Lei , Wu Hao Bin , Lou Xiong Wen 
Published: October 2013

AbstractHierarchically multishelled Fe(OH)3 microboxes are prepared by hydrothermal reaction of Fe4[Fe(CN)6]3 cubes with NaOH in EtOH/H2O (autoclave, 80 °C, 10 h) followed by annealing at 300 °C in air for 6 h.
ChemInform Abstract: Understanding the Surface Chemistry of Thiolate‐Protected Metallic Nanoparticles
Authors: Azcarate Julio C. , Corthey Gaston , Pensa Evangelina , Vericat Carolina , Fonticelli Mariano H. , Salvarezza Roberto C. , Carro Pilar 
Published: October 2013

AbstractReview: 120 refs.
ChemInform Abstract: 5‐Membered Heterocycles with Directly‐Bonded Sandwich and Half‐Sandwich Termini as Multi‐Redox Systems: Synthesis, Reactivity, Electrochemistry, Structure and Bonding
Authors: Hildebrandt Alexander , Pfaff Ulrike , Lang Heinrich 
Published: October 2013

AbstractReview: [synthesis, structure, bonding motif, reaction behavior, electrochem., spectroeectrochem.
ChemInform Abstract: Structure‐Reactivity Relationships for Aromatic Molecules: Electrostatic Potentials at Nuclei and Electrophile Affinity Indices
Authors: Galabov Boris , Ilieva Sonia , Koleva Gergana , Allen Wesley D. , Schaefer, Henry F. III , Schleyer Paul von R. 
Published: October 2013

AbstractReview: 91 refs.
Molecular phenotype of the foci in multifocal invasive breast carcinomas: Intertumoral heterogeneity is related to shorter survival and may influence the choice of therapy
Authors: Pekar Gyula , Gere Maria , Tarjan Miklos , Hellberg Dan , Tot Tibor 
Published: October 2013

BACKGROUNDMultiple synchronous, ipsilateral, invasive foci of breast carcinomas are frequent and are associated with a poorer prognosis. Few studies have investigated the prognostic and therapeutic implications of heterogeneity of such foci.METHODSThe authors reviewed the tumor type, grade, and size of all invasive foci in a series of 110 multifocal breast carcinomas documented on large‐format slides. Molecular phenotype was determined by immunohistochemistry in tissue microarray blocks using 3 classification systems. The survival of patients who had tumors with microscopic (tumor type and/or grade) heterogeneity and of those who had tumors with phenotypic heterogeneity was compared with the survival of patients who had multifocal homogeneous tumors using Kaplan‐Meier curves. The hazard ratio of dying from breast cancer was also calculated.RESULTSIntertumoral heterogeneity in tumor type and grade was detected in 16 of 110 tumors (14.6%) and in 6 of 110 tumors (5.5%), respectively. The molecular phenotype of invasive tumor foci within the same breast differed in 10% to 12.7% of patients (11‐14 of 110 tumors), depending on the classification system used. Patients who had phenotypically heterogeneous, multifocal cancers had a greater risk of dying from disease (HR=2.879; 95%CI=1.084−7.649; P = .034) and had significantly shorter survival (P = .016). Phenotypic differences were most common in patients who had tumors that were homogeneous in terms of tumor type (11 of 18 tumors) and histology grade (14 of 18 tumors). Phenotyping additional tumor foci had the potential to influence the therapeutic decisions in up to 8 patients.CONCLUSIONSPhenotyping more than 1 invasive focus of multifocal breast carcinomas only if the individual foci deviate microscopically appears to be insufficient, because phenotypic intertumoral heterogeneity may be observed in microscopically identical foci and has potential prognostic and therapeutic consequences. Cancer 2014;120:26–34. © 2013 American Cancer Society.
Intravenous aflibercept in patients with platinum‐resistant, advanced ovarian cancer: Results of a randomized, double‐blind, phase 2, parallel‐arm study
Authors: Tew William P. , Colombo Nicoletta , Ray‐Coquard Isabelle , del Campo Josep M. , Oza Amit , Pereira Deolinda , Mammoliti Serafina , Matei Daniela , Scambia Giovanni , Tonkin Katia , Shun Zhenming , Sternas Lars , Spriggs David R. 
Published: October 2013

BACKGROUNDIn this randomized phase 2 study, the authors assessed the efficacy and safety of intravenous aflibercept at 2 different doses (2 mg/kg or 4 mg/kg) in patients with recurrent, platinum‐resistant ovarian, peritoneal, or fallopian tube cancer who developed disease progression after receiving topotecan and/or pegylated liposomal doxorubicin.METHODSPatients were randomized to receive intravenous aflibercept at a dose of either 2 mg/kg or 4 mg/kg every 2 weeks until they developed disease progression or significant toxicity. The primary endpoint was to evaluate Response Evaluation Criteria in Solid Tumor response rates (overall response rate [ORR] = complete responses plus partial responses) and to test the null hypothesis (ORR, >5%). Secondary endpoints included time to tumor progression, safety, progression‐free survival/overall survival, drug pharmacokinetics, and immunogenicity. In total, 67 evaluable patients per cohort were planned based on a Simon 2‐stage design, and, if those patients responded, then enrollment could extend to 200 patients. Tumor radiographic response was assessed by investigators and by an independent review committee.RESULTSAfter the first 84 evaluable patients, 8 unconfirmed partial responders were noted (ORR, 10%) across both arms; the Independent Data Monitoring Committee recommended continuing blinded accrual. At study completion, 215 evaluable patients were accrued, including 1 responder of 106 patients (0.9%) in the 2‐mg/kg cohort and 5 responders of 109 patients (4.6%) in the 4‐mg/kg cohort according to the independent review committee. The clinical benefit rate (ORR plus stable disease >6 months) was 12.3% and 11% in the 2‐mg/kg and 4‐mg/kg cohorts, respectively. Treatment‐related grade 3 and 4 adverse events included hypertension (25.5% and 27.5% in the 2‐mg/kg and 4‐mg/kg cohorts, respectively), proteinuria (9.4% and 7.3%, respectively), and fatigue (5.7% and 3.7%, respectively). The gastrointestinal perforation rate was low (3 patients; 1.4%).CONCLUSIONSAflibercept at a dose of either 2 mg/kg or 4 mg/kg was generally well tolerated but did not meet the primary endpoint for response. Cancer 2014;120:335–343. © 2013 American Cancer Society.
Quality of life in patients with K‐RAS wild‐type colorectal cancer
Authors: Ringash Jolie , Au Heather‐Jane , Siu Lillian L. , Shapiro Jeremy D. , Jonker Derek J. , Zalcberg John R. , Moore Malcolm J. , Strickland Andrew , Kotb Rami , Jeffery Mark , Alcindor Thierry , Ng Siobhan , Salim Muhammad , Sabesan Sabe , Easaw Jay C. , Shannon Jenny , El‐Tahche Fabyolla , Walters Ian , Tu Dongsheng , O'Callaghan Christopher J. ,   NCIC Clinical Trials Group,   Australasian Gastrointestinal Trials Group
Published: October 2013

BACKGROUNDThe CO.20 trial randomized patients with K‐RAS wild‐type, chemotherapy‐refractory, metastatic colorectal cancer to receive cetuximab (CET) plus brivanib alaninate (BRIV) or CET plus placebo (CET/placebo).METHODSQuality of life (QoL) was assessed using the European Organization for Research and Treatment of Cancer Quality of Life Questionnaire C30 at baseline and at 2, 4, 6, 8, 12, 16, and 24 weeks until disease progression. Predefined coprimary QoL endpoints were time to deterioration (first worsening from baseline of ≥ 10 points) on the Physical Function (PF) and Global (GHS) scales.RESULTSOf 750 randomized patients, 721 (358 of whom received CET/BRIV) were assessable for QoL. QoL compliance and baseline PF and GHS scores did not differ by treatment arm. The median time to deterioration was 1.6 months versus 1.1 months for GHS (P = .02) and 5.6 months versus 1.7 months for PF (P < .0001) favoring CET/placebo. Secondary analysis favored CET/placebo for QOL response on the PF, Cognitive Function, Fatigue, Nausea, Appetite, and Diarrhea scales. A greater percentage of patients on the CET/BRIV arm had PF worsening at 6 weeks (31% vs 17%). Clinical adverse events of ≥ grade 3 were more common with CET/BRIV than with CET/placebo, including fatigue (25% vs 11%), hypertension, rash, diarrhea, abdominal pain, dehydration, and anorexia.CONCLUSIONSCompared with CET/placebo, the combination of CET/BRIV worsened time to QoL deterioration for patients with K‐RAS wild‐type, chemotherapy‐refractory, metastatic colorectal cancer on the PF and GHS scales of European Organization for Research and Treatment of Cancer Quality of Life Questionnaire C30. This result may be due to higher rates of fatigue and gastrointestinal adverse events. Cancer 2014;120:181–189. © 2013 American Cancer Society.
Cigarette smoking is associated with an increased risk of biochemical disease recurrence, metastasis, castration‐resistant prostate cancer, and mortality after radical prostatectomy
Authors: Moreira Daniel M. , Aronson William J. , Terris Martha K. , Kane Christopher J. , Amling Christopher L. , Cooperberg Matthew R. , Boffetta Paolo , Freedland Stephen J. 
Published: October 2013

BACKGROUNDThe current study was conducted to analyze the association between cigarette smoking and metastasis (the primary outcome) as well as time to biochemical disease recurrence (BCR), metastasis, castration‐resistant prostate cancer (CRPC), and prostate cancer‐specific and overall mortality (secondary outcomes) after radical prostatectomy among men from the Shared Equal Access Regional Cancer Hospital cohort.METHODSA retrospective analysis was performed of 1450 subjects for whom smoking status was available from preoperative notes. Analysis of baseline characteristics by smoking status was performed using the chi‐square and rank sum tests. The association between smoking status and time to the event was analyzed using Kaplan‐Meier plots, the log‐rank test, and Cox and competing risk models.RESULTSA total of 549 men (33%) men were active smokers and 1121 (67%) were nonsmokers at the time of surgery. Current smokers were younger and had a lower body mass index, higher prostate‐specific antigen level, and more extracapsular extension and seminal vesicle invasion (all P < .05). A total of 509 patients, 26 patients, 30 patients, 18 patients, and 217 patients, respectively, experienced BCR, metastasis, CRPC, prostate cancer‐related death, and any‐cause death over a median follow‐up of 62 months, 75 months, 61 months, 78 months, and 78 months, respectively. After adjusting for preoperative features, active smoking was found to be associated with an increased risk of BCR (hazards ratio [HR], 1.25; P = .024), metastasis (HR, 2.64; P = .026), CRPC (HR, 2.62; P = .021), and overall mortality (HR, 2.14; P < .001). Similar results were noted after further adjustment for postoperative features, with the exception of BCR (HR, 1.10; P = .335), metastasis (HR, 2.51; P = .044), CRPC (HR, 2.67; P = .015), and death (HR, 2.03; P < .001).CONCLUSIONSAmong patients undergoing radical prostatectomy, cigarette smoking was associated with an increased risk of metastasis. In addition, smoking was associated with a higher risk of BCR, CRPC, and overall mortality. If confirmed, these data suggest that smoking is a modifiable risk factor in patients with aggressive prostate cancer. Cancer 2014;120:197–204. © 2013 American Cancer Society.