5-溴甲基吲唑 | 496842-04-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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-溴甲基吲唑
• 中文别名: 5-(溴甲基)-1氢-吲唑；5-(溴甲基)-1H-吲唑氢溴酸盐
• 英文名称: 5-bromomethyl-1H-indazole
• 英文别名: 5-(bromomethyl)-1H-indazole
• CAS: 496842-04-7
• 化学式: C₈H₇BrN₂
• 分子量: 211.061
• InChiKey: ZTVQCRFGLVAFEC-UHFFFAOYSA-N

物化性质

• 沸点：
  355.8±17.0 °C(Predicted)
• 密度：
  1.694±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P264,P270,P271,P280,P304+P340,P305+P351+P338,P310,P330,P331,P363,P403+P233,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H314
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(Bromomethyl)-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-(Bromomethyl)-1H-indazole
CAS number: 496842-04-7

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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: C8H7BrN2
Molecular weight: 211.1

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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.

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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-溴甲基吲唑 在 吗啉 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 potassium peroxymonosulfate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 、 乙腈 为溶剂， 反应 64.0h， 生成 tert-butyl ((3RS,4SR,5SR)-5-((3-bromo-1H-indazol-5-yl)methyl)-4-hydroxy-1,1-dioxidotetrahydro-2H-thiopyran-3-yl)carbamate
  参考文献：
  名称：

  Discovery of Cyclic Sulfone Hydroxyethylamines as Potent and Selective β-Site APP-Cleaving Enzyme 1 (BACE1) Inhibitors: Structure-Based Design and in Vivo Reduction of Amyloid β-Peptides

  摘要：

  Structure-based design of a series of cyclic hydroxyethylamine BACE1 inhibitors allowed the rational incorporation of prime- and nonprime-side fragments to a central core template without any amide functionality. The core scaffold selection and the structure activity relationship development were supported by molecular modeling studies and by X-ray analysis of BACE1 complexes with various ligands to expedite the optimization of the series. The direct extension from P1-aryl- and heteroaryl moieties into the S3 binding pocket allowed the enhancement of potency and selectivity over cathepsin D. Restraining the design and synthesis of compounds to a physicochemical property space consistent with central nervous system drugs led to inhibitors with improved blood brain barrier permeability. Guided by structure-based optimization, we were able to obtain highly potent compounds such as 60p with enzymatic and cellular IC50 values of 2 and 50 nM, respectively, and with >200-fold selectivity over cathepsin D. Pharmacodynamic studies in APPS1/16 transgenic mice at oral doses of 180 mu mol/kg demonstrated significant reduction of brain A beta levels.

  DOI：

  10.1021/jm300069y
• 作为产物：
  描述：

  1-乙酰基-5-(乙酰氧基甲基)吲唑 在 氢溴酸 作用下， 以 水 为溶剂， 反应 16.0h， 以92%的产率得到5-溴甲基吲唑
  参考文献：
  名称：

  WO2008/82490

  摘要：

  公开号：

文献信息

• Therapeutic compounds for treating dyslipidemic conditions
  申请人：Adams D. Alan

  公开号：US20060178398A1

  公开（公告）日：2006-08-10

  The present invention relates to novel LXR ligands of Formula I and pharmaceutically acceptable salts, esters and tautomers thereof, which are useful in the treatment of dyslipidemic conditions, particularly depressed levels of HDL cholesterol.

  本发明涉及公式I的新型LXR配体及其药用盐、酯和互变异构体，可用于治疗脂质代谢异常症状，特别是降低HDL胆固醇水平。
• [EN] SUBSTITUTED 1H-INDAZOL-1-OL ANALOGS AS INHIBITORS OF BETA CATENIN/TCF PROTEIN-PROTEIN INTERACTIONS<br/>[FR] ANALOGUES SUBSTITUÉS DE 1H-INDAZOL-1-OL EN TANT QU'INHIBITEURS D'INTERACTIONS PROTÉINE-PROTÉINE BÊTA-CATÉNINE/TCF
  申请人：UNIV UTAH RES FOUND

  公开号：WO2013120045A1

  公开（公告）日：2013-08-15

  In one aspect, the invention relates to substituted lH-benzo[d][l,2,3]triazol-l-ol analgoues, derivatives thereof, and related compound; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders, e.g. various tumors and cancers, associated with β-catenin/Tcf protein- protein interaction dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，该发明涉及替代的1H-苯并[d][1,2,3]三唑-1-醇类似物，其衍生物以及相关化合物；制备这些化合物的合成方法；包括这些化合物的药物组合物；以及利用这些化合物和组合物治疗与β-连环蛋白/Tcf蛋白相互作用功能障碍相关的疾病，例如各种肿瘤和癌症的方法。本摘要旨在作为在特定领域进行搜索的扫描工具，并不打算限制本发明。
• [EN] 5-[(PIPERAZIN-1-YL)-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AS ADAMTS INHIBITORS FOR THE TREATMENT OF OSTEOARTHRITIS<br/>[FR] DÉRIVÉS 5-[(PIPÉRAZINE-1-YL) -3-OXO-PROPYL]-IMIDAZOLIDINE -2,4-DIONE COMME INHIBITEURS D'ADAMTS POUR LE TRAITEMENT DE L'ARTHROSE
  申请人：GALAPAGOS NV

  公开号：WO2016102347A1

  公开（公告）日：2016-06-30

  The present invention discloses compounds according to Formula (I), wherein R, R2, R3a, R3b, and Cy are as defined herein. The present invention discloses compounds inhibiting ADAMTS, methods for their production, pharmaceutical compositions comprising the same and methods for the prophylaxis and/or treatment of inflammatory conditions and/or diseases involving degradation of cartilage and/or disruption of cartilage homeostasis.

  本发明公开了根据式(I)的化合物，其中R、R2、R3a、R3b和Cy如本文所定义。本发明公开了抑制ADAMTS的化合物、其制备方法、包含该化合物的药物组合物以及用于预防和/或治疗涉及软骨降解和/或软骨稳态破坏的炎症状况和/或疾病的方法。
• Optimization of potency and pharmacokinetics of tricyclic indole derived inhibitors of HCV NS5B polymerase. Identification of ester prodrugs with improved oral pharmacokinetics
  作者：Srikanth Venkatraman、Francisco Velazquez、Stephen Gavalas、Wanli Wu、Kevin X. Chen、Anilkumar G. Nair、Frank Bennett、Yuhua Huang、Patrick Pinto、Yueheng Jiang、Oleg Selyutin、Bancha Vibulbhan、Qingbei Zeng、Charles Lesburg、Jose Duca、Larry Heimark、Hsueh-Cheng Huang、Sony Agrawal、Chuan-kui Jiang、Eric Ferrari、Cheng Li、Joseph Kozlowski、Stuart Rosenblum、Neng-Yang Shih、F. George Njoroge

  DOI：10.1016/j.bmc.2013.11.007

  日期：2014.1

  identified direct acting antivirals which have significantly improved cure rates in patients. Current efforts are directed towards identification of novel direct acting antiviral targeting different mechanism of actions which could become part of all oral therapies. We recently disclosed the identification of a novel tricyclic indole derived inhibitors of HCV NS5B polymerase that bound to the enzyme close

  在美国，HCV 感染是导致肝细胞癌和肝移植的主要原因。药物发现的最新进展已经确定了直接作用的抗病毒药物，这些药物显着提高了患者的治愈率。目前的努力是针对识别新的直接作用抗病毒药物，靶向不同的作用机制，这可能成为所有口服疗法的一部分。我们最近公开了一种新型三环吲哚衍生的 HCV NS5B 聚合酶抑制剂的鉴定，该抑制剂与靠近活性位点的酶结合。在这份手稿中，我们描述了对这些抑制剂的效力和药代动力学 (PK) 的进一步优化，以鉴定对 gt-1b 具有低 nM 效力的化合物。
• Rho kinase inhibitors
  申请人：——

  公开号：US20040138286A1

  公开（公告）日：2004-07-15

  A compound represented by the formula (1): 1 wherein R 1 —X— indicates that 1 to 4 R 1 —X— groups are present which may be the same or different, the ring A is a saturated or unsaturated 5-membered heterocyclic ring, X is a single bond, a group represented by the formula: —N(R 3 )—, —O— or —S—, or the like. R 1 is a hydrogen atom, a halogen atom, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group, or the like, R 2 is a hydrogen atom, a halogen atom, a nitro group, a carboxyl group, a substituted or unsubstituted alkyl group, or the like, and R 3 is a hydrogen atom, a substituted or unsubstituted alkyl group, or the like; a prodrug of said compound, or a pharmaceutically acceptable salt of said compound or prodrug is a useful compound as a therapeutic agent for diseases for which Rho kinase is responsible.

  化合物的化学式为（1）：1，其中R1—X—表示存在1到4个R1—X—基团，可以相同也可以不同，环A是饱和或不饱和的5元杂环，X是单键，一个由式子表示的基团：—N（R3）—，—O—或—S—等。R1是氢原子，卤素原子，硝基，羧基，取代或未取代的烷基或类似物，R2是氢原子，卤素原子，硝基，羧基，取代或未取代的烷基或类似物，R3是氢原子，取代或未取代的烷基或类似物；该化合物的前药或药物可接受的盐是治疗Rho激酶相关疾病的有用化合物。