5-bromo-2-methoxybenzenesulphonohydrazide | 23095-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-2-methoxybenzenesulphonohydrazide
• 英文别名: 5-bromo-2-methoxybenzenesulfonohydrazide；5-Brom-2-methoxy-benzolsulfonsaeurehydrazid
• CAS: 23095-06-9
• 化学式: C₇H₉BrN₂O₃S
• 分子量: 281.13
• InChiKey: HLIMZGRIEYXXCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-bromo-2-methoxybenzenesulphonohydrazide 、 (1,1,1-trifluoro-2-(trifluoromethyl)-but-2-yl)isocyanate 以 苯 为溶剂， 反应 1.0h， 以75%的产率得到2-((5-bromo-2-methoxyphenyl)sulfonyl)-N-(1,1,1-trifluoro-2-(trifluoromethyl)butan-2-yl)hydrazine-1-carboxamide
  参考文献：
  名称：

  1-芳酰基（1-芳基磺酰基）-4-二（三氟甲基）氨基脲烷基作为潜在的生理活性化合物

  摘要：

  1,1-双（三氟甲基）全氟异丁烯从（PFIB）获得的异氰酸烷基酯与芳酰基（芳基磺酰基）肼反应。合成了28种预期的具有生物活性的多氟化1,4-取代的氨基脲。每一个新产品的结构进行了分析和光谱法证实。利平斯基的年代和格洛瓦尼的参数，然后计算。两次调整的五个利平斯基的规则建议氟化候选药物。

  DOI：

  10.1016/j.jfluchem.2013.01.033
• 作为产物：
  描述：

  5-溴-2-甲氧基苯磺酰氯 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到5-bromo-2-methoxybenzenesulphonohydrazide
  参考文献：
  名称：

  1-芳酰基（1-芳基磺酰基）-4-二（三氟甲基）氨基脲烷基作为潜在的生理活性化合物

  摘要：

  1,1-双（三氟甲基）全氟异丁烯从（PFIB）获得的异氰酸烷基酯与芳酰基（芳基磺酰基）肼反应。合成了28种预期的具有生物活性的多氟化1,4-取代的氨基脲。每一个新产品的结构进行了分析和光谱法证实。利平斯基的年代和格洛瓦尼的参数，然后计算。两次调整的五个利平斯基的规则建议氟化候选药物。

  DOI：

  10.1016/j.jfluchem.2013.01.033

文献信息

• Sulphonohydrazides and related compounds. Part XI. Some substituted aryl ether sulphonhydrazides
  作者：R. J. W. Cremlyn、R. Hornby

  DOI：10.1039/j39690001341

  日期：——

  In a search for new pest control agents, the following benzenesulphonohydrazides have been prepared: 5-chloro-2-methoxy-, 3-chloro-4-methoxy-, 2-chloro-4-methoxy, 3-bromo-4-methoxy-, 5-bromo-2-methoxy-, 2-bromo-4-methoxy-, 4-methoxy-3-nitro-, 3,4-dimethoxy-, 2,5-dimethoxy-, 2,4-dimethoxy-, 3-acetamido-4-methoxy-, and 5-acetamido-2-methoxy-, In addition, 4-N-sulhonylhydrazinophenylacetic acid, and 4-N-sulphonyl

  为了寻找新的害虫防治剂，制备了以下苯磺酰肼：5-氯-2-甲氧基-，3-氯-4-甲氧基-，2-氯-4-甲氧基，3-溴-4-甲氧基- ，5-溴-2-甲氧基-，2-溴-4-甲氧基-，4-甲氧基-3-硝基-，3,4-二甲氧基-，2,5-二甲氧基-，2,4-二甲氧基-，3乙酰氨基-4-甲氧基，和5-乙酰氨基-2-甲氧基- ，另外，4- ñ -sulhonylhydrazinophenylacetic酸，和4- ñ -磺酰基肼基-2-甲氧基苯氧基乙酸已经制备。酰肼已被转化为许多衍生物（例如，酰肼，叠氮化物）。
• Synthesis of Sulfonated 5-Aminopyrazoles by I₂ /Benzoyl Peroxide-Mediated Tandem Reaction
  作者：Dongping Cheng、Tianpeng Chen、Xiaoliang Xu、Jizhong Yan

  DOI：10.1002/adsc.201701201

  日期：2018.3.1

  The tandem reaction of 3‐morpholinoacrylonitrile with sulfonyl hydrazides mediated by I2/benzoyl peroxide (BPO) is reported, which offers an efficient approach for the synthesis of sulfonated 5‐aminopyrazoles. It can bear a large scope of the substrates, and be used for the synthesis of aromatic, heteroaromatic and aliphatic sulfonated 5‐aminopyrazoles.

  据报道，由I 2 /过氧化苯甲酰（BPO）介导的3-吗啉代丙烯腈与磺酰肼的串联反应，为合成磺化的5-氨基吡唑提供了一种有效的方法。它可以承受很大范围的底物，并用于合成芳族，杂芳族和脂族磺化5-氨基吡唑。
• [EN] SULFONYL SEMICARBAZIDES, SEMICARBAZIDES AND UREAS, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS FOR TREATING HEMORRHAGIC FEVER VIRUSES, INCLUDING INFECTIONS ASSOCIATED WITH ARENAVIRUSES<br/>[FR] SULFONYL SEMICARBAZIDES, SEMICARBAZIDES ET URÉES, COMPOSITIONS PHARMACEUTIQUES À BASE DE CEUX-CI, ET PROCÉDÉS DE TRAITEMENT DES VIRUS RESPONSABLES DES FIÈVRES HÉMORRAGIQUES, COMPRENANT DES INFECTIONS ASSOCIÉES À DES ARÉNAVIRUS
  申请人：SIGA TECHNOLOGIES INC

  公开号：WO2012060820A1

  公开（公告）日：2012-05-10

  Compounds, methods and pharmaceutical compositions for treating viral infections, by administering certain novel semicarbazides, sulfonyl carbazides, ureas and related compounds in therapeutically effective amounts are disclosed. Methods for preparing the compounds and methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment and prophylaxis of viral infections such as caused by hemorrhagic fever viruses is disclosed, i.e., including but not limited to Arenaviridae (Junin, Machupo, Guanavito, Sabia and Lassa), Filoviridae (ebola and Marburg viruses), Flaviviridae (yellow fever, omsk hemorrhagic fever and Kyasanur Forest disease viruses), and Bunyaviridae (Rift Valley fever).

  本文揭示了利用某些新型半卡巴肼、磺酰基卡巴肼、脲及相关化合物以治疗病毒感染的复合物、方法和制药组合物，通过在治疗有效量下给药。本文还揭示了制备这些化合物的方法以及使用这些化合物和其制药组合物的方法。具体而言，揭示了治疗和预防由出血热病毒引起的病毒感染，包括但不限于Arenaviridae（Junin，Machupo，Guanavito，Sabia和Lassa），Filoviridae（埃博拉和马尔堡病毒），Flaviviridae（黄热病，奥木斯克出血热和Kyasanur Forest病毒）以及Bunyaviridae（裂谷热）。
• Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of neurodegenerative diseases
  申请人：Bora Martin Keenan

  公开号：US20050004167A1

  公开（公告）日：2005-01-06

  The invention relates to BCAT inhibitor compounds of formula (I) and use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, neuropathic pain, Parkinson's disease, diabetic retinopathy, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.

  本发明涉及公式（I）的BCAT抑制剂化合物及其用于治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元丢失，以及治疗神经退行性疾病，包括阿尔茨海默病、肌萎缩性侧索硬化症、亨廷顿病和唐氏综合症，治疗或预防兴奋性氨基酸过度刺激的不良后果，治疗焦虑、精神病、惊厥、氨基糖苷类抗生素引起的听力损失、偏头痛、慢性疼痛、神经病性疼痛、帕金森病、糖尿病视网膜病变、青光眼、巨细胞病毒性视网膜炎、尿失禁、阿片类耐受或戒断，以及诱导麻醉和增强认知功能。
• Optimization and structure–activity relationships of a series of potent inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase as novel antimicrobial agents
  作者：Nag S. Kumar、Emily A. Amandoron、Artem Cherkasov、B. Brett Finlay、Huansheng Gong、Linda Jackson、Sukhbir Kaur、Tian Lian、Anne Moreau、Christophe Labrière、Neil E. Reiner、Raymond H. See、Natalie C. Strynadka、Lisa Thorson、Edwin W.Y. Wong、Liam Worrall、Roya Zoraghi、Robert N. Young

  DOI：10.1016/j.bmc.2012.10.002

  日期：2012.12

  A novel series of hydrazones were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK has been identified as one of the most highly connected 'hub proteins' in MRSA. PK has been shown to be critical for bacterial survival which makes it a potential target for development of novel antibiotics and the high degree of connectivity implies it should be very sensitive to mutations and thus less able to develop resistance. PK is not unique to bacteria and thus a critical requirement for such a PK inhibitor would be that it does not inhibit the homologous human enzyme(s) at therapeutic concentrations. Several MRSA PK inhibitors (including 8d) were identified using in silico screening combined with enzyme assays and were found to be selective for bacterial enzyme compared to four human PK isoforms (M1, M2, R and L). However these lead compounds did not show significant inhibitory activity for MRSA growth presumably due to poor bacterial cell penetration. Structure-activity relationship (SAR) studies were carried out on 8d and led us to discover more potent compounds with enzyme inhibiting activities in the low nanomolar range and some were found to effectively inhibit bacteria growth in culture with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. These inhibitors bind in two elongated flat clefts found at the minor interfaces in the homo-tetrameric enzyme complex and the observed SAR is in keeping with the size and electronic constraints of these binding sites. Access to the corresponding sites in the human enzyme is blocked. (C) 2012 Elsevier Ltd. All rights reserved.