5-溴-3-碘-1H-吲唑 | 459133-66-5

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-溴-3-碘-1H-吲唑
• 中文别名: 5-溴-3-碘-吲唑
• 英文名称: 5-bromo-3-iodo-1H-indazole
• 英文别名: 5-bromo-3-iodo-2H-indazole
• CAS: 459133-66-5
• 化学式: C₇H₄BrIN₂
• 分子量: 322.931
• InChiKey: IBFAYUXCRDDBRD-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C(Solv: ligroine (8032-32-4))
• 沸点：
  413.1±25.0 °C(Predicted)
• 密度：
  2.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-3-iodo-1H-indazole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Bromo-3-iodo-1H-indazole
CAS number: 459133-66-5

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C7H4BrIN2
Molecular weight: 322.9

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide, hydrogen Iodide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-溴-3-碘-1H-吲唑 在 copper(l) iodide 、 四(三苯基膦)钯 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 (R)-2-[5-(3-methylsulfanyl-1H-indazol-5-yl)pyridin-3-ylamino]-2-phenylethanol
  参考文献：
  名称：

  [EN] NOVEL BI-RING PHENYL-PYRIDINES/PYRAZINES FOR THE TREATMENT OF CANCER
  [FR] NOUVELLES PHÉNYLPYRIDINES/PYRAZINES À DEUX CYCLES POUR LE TRAITEMENT DU CANCER

  摘要：

  该发明提供了具有以下一般式的新化合物：其中R1、R2和R3如本文所述，包括该化合物的组合物以及使用该化合物的方法。

  公开号：

  WO2014090692A1
• 作为产物：
  描述：

  5-溴-2-氟苯甲醛 在 碘 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-溴-3-碘-1H-吲唑
  参考文献：
  名称：

  A novel series of indazole-/indole-based glucagon receptor antagonists

  摘要：

  A novel, potent series of glucagon receptor antagonists (GRAs) was discovered. These indazole-and indole-based compounds were designed on an earlier pyrazole-based GRA lead MK-0893. Structure-activity relationship (SAR) studies were focused on the C3 and C6 positions of the indazole core, as well as the benzylic position on the N-1 of indazole. Multiple potent GRAs were identified with excellent in vitro profiles and good pharmacokinetics in rat. Among them, GRA 16d was found to be orally active in blunting glucagon induced glucose excursion in an acute glucagon challenge model in glucagon receptor humanized (hGCGR) mice at 1, 3 and 10 mg/kg (mpk), and significantly lowered acute glucose levels in hGCGR ob/ob mice at 3 mpk dose. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.015
• 作为试剂：
  描述：

  氢氧化钾 、 5-溴吲唑 、 碘 在 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 5-溴-3-碘-1H-吲唑 作用下， 以 N,N-二甲基甲酰胺 、 ice water 为溶剂， 反应 12.0h， 以to provide the desired product of 5-bromo-3-iodo-1H-indazole (8 g, yield: 90.0%)的产率得到5-溴-3-碘-1H-吲唑
  参考文献：
  名称：

  SUBSTITUED BENZOFURAN COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

  摘要：

  本发明涉及式（I）的化合物，这些化合物可用作丙型肝炎病毒（HCV）NS5B聚合酶抑制剂，以及这些化合物的合成，以及使用这些化合物来抑制HCV NS5B聚合酶活性，治疗或预防HCV感染，并在细胞系统中抑制HCV病毒复制和/或病毒产生。

  公开号：

  US20150246902A1

文献信息

• Discovery of a 3-(4-Pyrimidinyl) Indazole (MLi-2), an Orally Available and Selective Leucine-Rich Repeat Kinase 2 (LRRK2) Inhibitor that Reduces Brain Kinase Activity
  作者：Jack D. Scott、Duane E. DeMong、Thomas J. Greshock、Kallol Basu、Xing Dai、Joel Harris、Alan Hruza、Sarah W. Li、Sue-Ing Lin、Hong Liu、Megan K. Macala、Zhiyong Hu、Hong Mei、Honglu Zhang、Paul Walsh、Marc Poirier、Zhi-Cai Shi、Li Xiao、Gautam Agnihotri、Marco A. S. Baptista、John Columbus、Matthew J. Fell、Lynn A. Hyde、Reshma Kuvelkar、Yinghui Lin、Christian Mirescu、John A. Morrow、Zhizhang Yin、Xiaoping Zhang、Xiaoping Zhou、Ronald K. Chang、Mark W. Embrey、John M. Sanders、Heather E. Tiscia、Robert E. Drolet、Jonathan T. Kern、Sylvie M. Sur、John J. Renger、Mark T. Bilodeau、Matthew E. Kennedy、Eric M. Parker、Andrew W. Stamford、Ravi Nargund、John A. McCauley、Michael W. Miller

  DOI：10.1021/acs.jmedchem.7b00045

  日期：2017.4.13

  set out to develop LRRK2 inhibitors to test this hypothesis. A high throughput screen of our compound collection afforded a number of promising indazole leads which were truncated in order to identify a minimum pharmacophore. Further optimization of these indazoles led to the development of MLi-2 (1): a potent, highly selective, orally available, brain-penetrant inhibitor of LRRK2.

  富含亮氨酸的重复激酶2（LRRK2）是一种大型的多结构域蛋白，除其他区域外，还包含一个激酶结构域和GTPase结构域。具有在激酶结构域中获得功能突变（例如最普遍的G2019S突变）的个体与帕金森氏病（PD）发生的风险增加相关。鉴于这种抑制LRRK2激酶活性作为影响疾病进展的潜在手段的基因验证，我们的团队着手开发LRRK2抑制剂来验证这一假设。我们化合物收集物的高通量筛选提供了许多有前途的吲唑线索，这些线索被截短以鉴定最小的药效团。这些吲唑的进一步优化导致MLi-2（1）：一种有效的，高度选择性的，口服可得的LRRK2脑渗透抑制剂。
• Synthesis of 3-Indazolecarboxylic Esters and Amides via Pd-Catalyzed Carbonylation of 3-Iodoindazoles
  作者：Hans-Peter Buchstaller、Kai Wilkinson、Kasimir Burek、Yasmin Nisar

  DOI：10.1055/s-0030-1260199

  日期：2011.10

  A straightforward and effective procedure for the preparation of 1H-indazole-3-carboxylic acid esters and amides was developed. A series of functionalized 3-iodoindazoles were subjected to Pd-catalyzed carbonylations in the presence of methanol or amines, yielding the title compounds in moderate to good yield. For the majority of examples, the reaction proceeded cleanly under mild conditions, which

  开发了一种简单有效的制备1 H-吲哚-3-羧酸酯和酰胺的方法。在甲醇或胺的存在下，对一系列官能化的3-碘吲唑进行Pd催化的羰基化反应，以中等至良好的收率得到标题化合物。对于大多数实例，反应在温和条件下干净地进行，该条件易于被允许进一步合成转化的多种官能团所耐受。 羰基化-酯-酰胺-烷氧基羰基化-氨基羰基化-碘吲唑-钯催化
• [EN] KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME<br/>[FR] INHIBITEURS DE KINASES ET PROCÉDÉ DE TRAITEMENT DU CANCER UTILISANT CEUX-CI
  申请人：UNIV HEALTH NETWORK

  公开号：WO2011123937A1

  公开（公告）日：2011-10-13

  The present teachings provide a compound represented by Strutural Formula (I): or a pharmaceutically acceptable salt thereof. Also described are a pharmaceutical composition and method of use thereof.

  本教学提供了一种由结构式(I)表示的化合物，或其药用可接受的盐。还描述了一种药物组合物及其使用方法。
• [EN] 5-AMINO-4-HYDROXY-7-(1H-INDOLMETHYL)-8-METHYLNONAMIDE DERIVATIVES AS RENIN INHIBITORS FOR THE TREATMENT OF HYPERTENSION<br/>[FR] DERIVE DE 5-AMINO-4-HYDROXY-7-(1H-INDOLMETHYL)-8-METHYLNONAMIDE UTILISES EN TANT QU'INHIBITEURS DE RENINE DANS LE TRAITEMENT DE L'HYPERTENSION
  申请人：SPEEDEL EXPERIMENTA AG

  公开号：WO2005090305A1

  公开（公告）日：2005-09-29

  The application relatés to novel alkanamides of the general formula (I) where X is -CH2- or >CH-OH; (A) R1 is e.g. an optionally substituted heterocyclyl radical or an optionally substituted polycyclic, unsaturated hydrocarbon radical where X is hydroxymethylene; R2 is C1-C6-alkyl or C3-C6-cydoalkyl; R3 are each independently H, C1-C6-alkyl, C1-6-alkoxycarbonyl or C1-C6-alkanoyl; R4 is C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl or unsubstituted or substituted aryl­C1-C6-alkyl; R5 is Cl-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkanoyloxy­ C1-C6-alkyl, C1-C6-aminoalkyl, C1-C6-alkylamino-C1-C6-alkyl, C1-C6-dialkylamino-Cl-C6-alkyl, C1-C6-alkanoylamido-C1-C6-alkyl, HO(O)C-C1-C6-alkyl, C1-C6-alkyl-O-(O)C-C1-C6-alkyl, H2N-C(O)-C1-C6-alkyl, C1-C6-alkyl-HN-C(O)-C1-C6-alkyl, (C1,-C6-alkyl)2N-C(O)-C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, cyano-C1-C6-alkyl, halo-Cl-C6-alkyl, optionally substituted aryl-­Co-C6-alkyl, optionally substituted C3-C8-cycloalkyl-Co-C6-alkyl or optionally substituted heterocydyl-Co-C6-alkyl; to a process for their preparation and to the use of these compounds as medicines, especially as renin inhibitors for the treatment of hypertension.

  该申请涉及一般式（I）的新型烷酰胺，其中X为-CH2-或>CH-OH；（A）R1例如是一个可选择取代的杂环基团或一个可选择取代的多环不饱和碳氢基团，其中X为羟甲基；R2为C1-C6-烷基或C3-C6-环烷基；R3各自独立地为H、C1-C6-烷基、C1-6-烷氧羰基或C1-C6-烷酰基；R4为C1-C6-烷基、C3-C6-环烷基、C2-C6-烯基或未取代或取代的芳基-C1-C6-烷基；R5为Cl-C6-烷基、C1-C6-羟基烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷酰氧基-C1-C6-烷基、C1-C6-氨基烷基、C1-C6-烷基氨基-C1-C6-烷基、C1-C6-二烷基氨基-Cl-C6-烷基、C1-C6-烷酰胺基-C1-C6-烷基、HO(O)C-C1-C6-烷基、C1-C6-烷基-O-(O)C-C1-C6-烷基、H2N-C(O)-C1-C6-烷基、C1-C6-烷基-HN-C(O)-C1-C6-烷基、（C1,-C6-烷基）2N-C(O)-C1-C6-烷基、C2-C8-烯基、C2-C8-炔基、氰基-C1-C6-烷基、卤代Cl-C6-烷基、可选择取代的芳基-Co-C6-烷基、可选择取代的C3-C8-环烷基-Co-C6-烷基或可选择取代的杂环基-Co-C6-烷基；以及它们的制备方法和将这些化合物用作药物的用途，特别是作为肾素抑制剂治疗高血压。
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSES ORGANIQUES
  申请人：SPEEDEL EXPERIMENTA AG

  公开号：WO2005090304A1

  公开（公告）日：2005-09-29

  The invention relates to novel amino alcohols of the general formula (I) where X, R1, R2, R3, R4, R5 and R6 are each as defined in detail in the description, to a process for their preparation and to the use of these compounds as medicines, in particular as renin inhibitors.

  这项发明涉及一般式(I)的新型氨基醇，其中X、R1、R2、R3、R4、R5和R6的定义详细描述在说明书中，以及它们的制备方法和将这些化合物用作药物，特别是作为肾素抑制剂。