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Phosphine-Relayed Aldehyde-Olefination and Aza-Wittig Reaction with 2,2,2-Trifluorodiazoethane

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Chinese Journal of Chemistry 2018年第8期36卷 723-730页

作者： Fa-Guang Zhang Ning Lv Yan Zheng Jun-An Ma Department of Chemistry Tianjin Key Laboratory of Molecular Optoelectronic Sciences and Tianjin Collaborative Innovation Center of Chemical Science & Engineering Tianjin University Tianjin 300072 China

Phosphine-relayed olefination and aza-Wittig reactions of readily available aldehydes with 2,2,2-trifluorodiazoethane （CF3CHN2） have been realized. This protocol enables the facile construction of a series of triflu... 详细信息

关键词： diazo compounds olefination Wittig reactions 2,2,2-trifluorodiazoethane phosphine

Aryl Diazonium Salt-Triggered Cyclization a nd Cycloaddition Reactions: Past, Present, and Future

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Chinese Journal of Chemistry 2020年第10期38卷 1132-1152页

作者： Fa-Guang Zhang Zhen Chen Chi Wai Cheung Jun-An Ma Department of Chemistry Tianjin Key Laboratory of Molecular Optoelectronic SciencesFrontiers Science Center for Synthetic Biology(Ministry of Education)and Tianjin Collaborative Innovation Center of Chemical Science&EngineeringTinjin UniversityTianjin 300072China Joint School of National University of Singapore and Tianjin University International Campus of Tianjin UniversityBinhai New CityFuzhou 350207FujianChina

Aryl diazonium salts occupy a privileged role in synthetic chemistry owing to their ready availability and versatile reactivity.While their applications in accessing diversely functionalized arene derivatives via denitrogenation-coupling and reduction/addition reactions have been well recognized by practitioners in both academia and industry,recent renaissance in chemical transformations of retaining the key N2-unit has emerged as a powerful technique to construct various A/-heterocycles.This review covers the history and latest advances in cyclization and cycloaddition reactions using aryl diazonium salts as N2-annulation synthons.The scope,applications,and opportunities in exploring new chemical space by this sustainable strategy are summarized and discussed.

关键词： salts summarized retaining

Pd（Ⅱ）-Catalyzed Phosphorylation of Enamido C（sp^2）-H Bonds： A General Route to β-Amido-vinylphosphonates

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Chinese Journal of Chemistry 2018年第9期36卷 809-814页

作者： Baokun qiao Hao-qiang Cao Yin-Jun Huang Yue zhang Jing Nie Fa-Guang Zhang Jun-An Ma Department of Chemistry Tianjin Key Laboratory of Molecular Optoelectronic Sciences and Tianjin Collaborative Innovation Center of Chemical Science & Engineering Tianjin University Tianjin 300072 China

Organophosphorus compounds are essential structures in modern pharmaceutical, agrochemical, and material sciences. The development of new and efficient methods for the synthesis of C-P bonds has been an important focus of research. We herein report a Pd-catalyzed enamido C（sp2）-H phosphorylation for direct construction of C-P bonds under simple and convenient conditions without the need for additional ligands or directing groups. The present reaction can tolerate a wide range of functional groups, and furnish a variety of phosphorylation products including tetrasubstituted-vinyl β-aminophosphonates that are otherwise difficult to access. This protocol was also exemplified into the late-stage modification of bioactive natural prod- ucts and was suitable for large-scale synthesis.

关键词： C-H activation phosphorylation palladium catalysis enamines late-stage functionalization

Effects of 5-hydroxytryptamine and 5-hydroxytryptamine 2A/2C agonist on the genioglossus activity and sleep apnea in rats

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Chinese Medical Journal 2010年第15期123卷 2094-2098页

作者： ZHONG Yi-jue zhang Cheng WANG guang-fa Department of Pulmonary Medicine Peking University First Hospital Beijing 100034China

Background 5-hydroxytryptamine （5-HT） is a common neurotransmitter in the brain which plays an important role in the pathogenesis of sleep apnea.Dysfunction of 5-HT and 5-HT2 receptors may lead to the collapse of the upper airway and the instability of respiratory control, which in turn produce apnea.Genioglossus （GG） is one of the most important oropharyngeal muscles maintaining the upper airway open.The present study aimed to investigate the effects of 5-HT and 5-HT2 receptor on GG activity and the sleep apnea in Sprague-Dawley （SD） rats.Methods Microinjection probes were placed within the fourth ventricle of sixteen SD rats.After recovery for a week, the electromyogram （EMG） of GG was recorded in the anesthetized and vagotomized rats.The changes of GG activity before and after the microinjection of 5-HT or 5-HT2A/2c agonist -2,5-dimethoxy-4-iodoamphetamine hydrochloride （DOI）were observed.Probes were also laid in another eight SD rats.Electroencephalogram （EEG）, EMG of neck muscle and respiration were recorded at the same time a week later.The effects of DOI on the occurrence of sleep apnea were explored.Results Both 5-HT and DOI significantly enhanced the activity of GG just 3 minutes after the completion of injection.The effect of 5-HT disappeared quickly and the effect of DOI lasted for more than 27 minutes.DOI also significantly decreased the post-sigh apnea index in non-rapid-eye-movement （NREM） and rapid-eye-movement （REM） sleep and decreased the spontaneous apnea index only in NREM sleep （P 〈0.05, respectively）.Conclusion 5-HT and 5-HT2A/2c system correlated closely with the pathogenesis of the sleep apnea syndrome and 5-HT receptors may become the target of the drug treatment.

关键词： serotonin 5-hydroxytryptamine2A/2C rat sleep apnea genioglossus

Pulmonary embolism and deep vein thrombosis caused by nitrous oxide abuse: A case report

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World Journal of Clinical Cases 2019年第23期7卷 4057-4062页

作者： Wen Sun Ji-Ping Liao Yan Hu Wei zhang Jing Ma guang-fa Wang Department of Pulmonary and Critical Care Medicine Peking University First Hospital

BACKGROUND Nitrous oxide(N2O)has gained increasing popularity as a recreational drug,causing hallucinations,excitation,and psychological dependence.However,side effects have been reported in recent years.Our case report proposes a correlation among N2O,pulmonary embolism(PE),and deep vein thrombosis(DVT)and emphasizes the role of homocysteine(Hcy)in thrombotic events.CASE SUMMARY A 29-year-old man with long-term N2O abuse sought evaluation after acute chest pain.A diagnostic workup revealed PE,DVT,and hyperhomocysteinemia.The patient was successfully treated with thrombolytic and anticoagulant therapy.Moreover,his Hcy level decreased and returned to normal after Hcy-lowering therapy.CONCLUSION Chronic N2O abuse might increase the risk of PE and DVT,although there have been few studies previously.

关键词： Nitrous oxide Pulmonary embolism Deep vein thrombosis Homocysteine Case report

Transorbital nonmissile penetrating brain injury: Report of two cases

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World Journal of Clinical Cases 2020年第2期8卷 471-478页

作者： Hang Xue Wei-Tao zhang guang-Ming Wang Lin Shi Yi-Ming zhang Hong-fa Yang Department of Neurotraumatic Surgery The First Hospital of Jilin UniversityChangchun 130021Jilin ProvinceChina Department of Neurosurgery The Affiliated Hospital of Changchun University of Traditional Chinese MedicineChangchun 130021Jilin ProvinceChina Department of Neurosurgery Qilu Hospital of Shandong UniversityJi’nan 250002Shandong ProvinceChina

BACKGROUND Penetrating brain injury(PBI) is an uncommon emergency in neurosurgery, and transorbital PBI is a rare type of PBI. Reasonable surgical planning and careful postoperative management can improve the prognosis of patients CASE SUMMARY The first case is a 68-year-old male patient who was admitted to the hospital because a branch punctured his brain through the orbit for approximately 9 h after he unexpectedly fell while walking. After admission, the patient underwent emergency surgical treatment and postoperative anti-infection treatment. The patient was able to follow instructions at a 4-mo follow-up review. The other case is a 46-year-old male patient who was admitted to the hospital due to an intraorbital foreign body caused by a car accident, after which the patient was unconscious for approximately 6 h. After admission, the patient underwent emergency surgical treatment and postoperative anti-infection treatment. The patient could correctly answer questions at a 3-mo follow-up review.CONCLUSION Transorbital PBI is a rare and acute disease. Early diagnosis, surgical intervention, and application of intravenous antibiotics can improve the prognosis and quality of life of patients.

关键词： Transorbital Nonmissile Penetrating brain injury Foreign body Case report

Chemical analysis and in vitro antimicrobial effects and mechanism of action of Trachyspermum copticum essential oil against Escherichia coli

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Asian Pacific Journal of Tropical Medicine 2017年第7期10卷 726-732页

作者： Wei Huang Jian-Qing Wang Hai-Yan Song Qian zhang guang-fa Liu Tianjin University of Science & Technology China Packaging Research&Test Center

Objective: To find a natural plant essential oil(EO) with excellent antimicrobial effect on food-borne bacteria and to explore the mechanism of its antimicrobial function against Escherichia coli(E. coli). Methods: The antimicrobial activity of seven EOs against Gramnegative E. coli ATCC 8739 and Gram-positive Staphylococcus aureus ATCC 6538 was investigated using agar disk diffusion method, and the minimum inhibitory concentration(MIC) and minimum bactericidal concentration(MBC) of each EO was determined using the broth dilution method. The chemical composition of the Trachyspermum copticum(T. copticum) EO was analyzed using gas chromatography–mass spectrometry(GC/MS). In order to explore the mechanism of the antimicrobial action, 1 MIC and 2 MIC of T. copticum EO was added to a suspension of E. coli, the growth curve and the scanning electron microscopy(SEM) analysis of E. coli, and the release of cell constituents and protein and potassium ions from the bacterial cell were measured. Results: The T. copticum EO had the best antimicrobial activity against the test bacteria, and 10 compounds accounting for 94.57% of the total oil were identified, with the major components being thymol(46.22%), p-cymene(19.03%), and 毭-terpinene(22.41%). The addition of 1 MIC T. copticum EO significantly inhibited the growth of E. coliand increased the release of cell constituents and protein and potassium ions from the bacterial cells. Scanning electron micrographs showed that T. copticum EO caused most of the E. colicell membranes to collapse and rupture, leading to cell death. Conclusions: These results indicate that T. copticum EO is a good natural antimicrobial agent for food-borne pathogens.

关键词： Essential oil Trachyspermum copticum Antimicrobial activity GC/MS Escherichia coli Mechanism

Clinical Manifestations of Fibrosing Mediastinitis in Chinese Patients

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Chinese Medical Journal 2016年第22期129卷 2697-2702页

作者： Yan Hu Jian-Xing Qiu Ji-Ping Liao Hong zhang Zhe Jin guang-fa Wang Department of Respiratory and Critical Care Medicine Peking University First Hospital Beijing 100034 China Department of Medical Imaging Peking University First Hospital Beijing 100034 China

Background：Fibrosing mediastinitis （FM） is a rare disease.FM is thought to be related to prior granulomatous mediastinal infection,such as histoplasmosis or tuberculosis.The majority of cases have been reported in endemic regions for histoplasmosis.The characteristics of cases of FM in China,where the prevalence of tuberculosis is high,have not been reported.We analyzed the clinical,imaging,and bronchoscopic features of Chinese patients with FM to promote awareness of this disease.Methods：Between January 2005 and June 2015,twenty patients were diagnosed with FM in our hospital.Medical records and follow-up data were collected.Imaging and biopsy findings were reviewed by radiologists and pathologists.Results：A total of 20 patients were analyzed （8 males and 12 females）.The age ranged from 43 to 88 years with a mean age of 69.5 years.Previous or latent tuberculosis was found in 12 cases.Clinical symptoms included dyspnea （18/20）,cough （17/20）,expectoration （7/20）,and recurrent pneumonia （3/20）.Chest computed tomography scans showed a diffuse,homogeneous,soft tissue process throughout the mediastinum and hila with compression of bronchial and pulmonary vessels.Calcification was common （15/20）.Pulmonary hypertension was present in 9 of 20 cases.Diffuse black pigmentation in the bronchial mucosa was frequently seen on bronchoscopy （12/13）.The patients＇ response to antituberculosis treatment was inconsistent.Conclusions：FM in Chinese patients is most likely associated with tuberculosis.Some characteristics of FM are different from cases caused by histoplasmosis.

关键词： Mediastinitis Sclerosis Tuberculosis

Dual Incorporation of Trifluoromethyl and Cyano Groups into Pyrazole Pharmcophores via Silver-Catalyzed Cycloaddition Reaction of Trifluorodiazoethane

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CCS Chemistry 2022年第12期4卷 3693-3704页

作者： Cheng-Feng Gao Yin Zhou Hai Ma Yue zhang Jing Nie Fa-Guang Zhang Jun-An Ma Department of Chemistry Tianjin Key Laboratory of Molecular Optoelectronic SciencesFrontiers Science Center for Synthetic BiologyMinistry of EducationTianjin Collaborative Innovation Centre of Chemical Science and EngineeringTianjin UniversityTianjin 300072 Institute of Chinese Materia Medica China Academy of Chinese Medical SciencesBeijing 100700

The dual incorporation of two important functional groups—trifluoromethyl and cyano moieties into one heterocyclic core in a single-step reaction represents an appealing but largely unaddressed synthetic challenge.Here we demonstrate that a silver-catalyzed[3+2]cycloaddition reaction of dicyanoalkenes with trifluorodiazoethane(CF_(3)CHN2)could render a facile construction of a unique category of pyrazoles that are simultaneously adorned by trifluoromethyl and cyano groups.Changing the location pattern of the cyano group in starting dicyanoalkene material allows regiodivergent access to two series of previously elusive trifluoromethyl cyanopyrazoles with an exquisite level of regiocontrol.Thus,this method could be applied in the preparation of cyano-analogues of CF_(3)-containing drugs(Celecoxib)and agrochemicals(Penthiopyrad and Fluazolate).Notably,several cyano-analogues of Celecoxib demonstrate enhanced inhibitory activity towards cyclooxygenase-2(COX-2),thereby laying a good foundation for developing new lead-based antiinflammatory agents.

关键词： pyrazoles trifluoromethyl group cyano group silver catalysis diazo reagents