3-(4-硝基苯基)金刚烷-1-羧酸 | 7123-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-硝基苯基)金刚烷-1-羧酸
• 中文别名: 3-(4-硝基苯基)金刚烷-1-甲酸
• 英文名称: 3-(4-nitrophenyl)-1-adamantanecarboxylic acid
• 英文别名: 3-(4-nitrophenyl)adamantane-1-carboxylic acid；1-(p-Nitrophenyl)-adamantan-3-carbonsaeure；1-(4-Nitro-phenyl)-adamantan-3-carbonsaeure
• CAS: 7123-76-4
• 化学式: C₁₇H₁₉NO₄
• mdl: MFCD00188065
• 分子量: 301.342
• InChiKey: JGYFFTQRRDPOIR-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 密度：
  1.387±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2916399090

SDS

Name:	3-(4-Nitrophenyl)adamantane-1-carboxylic acid 97% Material Safety Data Sheet
Synonym:
CAS:	7123-76-4

Section 1 - Chemical Product MSDS Name:3-(4-Nitrophenyl)adamantane-1-carboxylic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7123-76-4	3-(4-Nitrophenyl)adamantane-1-carboxyl	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 7123-76-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 197 - 200 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C17H19NO4
Molecular Weight: 301

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7123-76-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(4-Nitrophenyl)adamantane-1-carboxylic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 7123-76-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 7123-76-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7123-76-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯基)金刚烷-1-羧酸 以93%的产率得到3-(4-nitrophenyl)-1-adamantanecarbonitrile
  参考文献：
  名称：

  1-(adamantyl)amidines and their use in the treatment of conditions generally associated with abnormalities in glutamatergic transmission

  摘要：

  1-(戊二醇基)胺基甲酸盐类化合物及其在治疗通常与谷氨酸能传递异常相关的疾病中的用途。

  公开号：

  US06500866B1
• 作为产物：
  描述：

  1-苯基金刚烷 在 硫酸 、 溴 、 硝酸 作用下， 生成 3-(4-硝基苯基)金刚烷-1-羧酸
  参考文献：
  名称：

  Stepanov,F.N. et al., Journal of Organic Chemistry USSR (English Translation), 1966, vol. 2, p. 640 - 643

  摘要：

  DOI：

文献信息

• Adamantyl- and other polycyclic cage-based conjugates of desferrioxamine B (DFOB) for treating iron-mediated toxicity in cell models of Parkinson’s disease
  作者：Thomas J. Telfer、Jeffrey R. Liddell、Clare Duncan、Anthony R. White、Rachel Codd

  DOI：10.1016/j.bmcl.2017.03.001

  日期：2017.4

  facilitate intracellular iron sequestration. The first activity screen showed compounds with methyl-substituted adamantyl (1-3), noradamantyl (5), or 1-pentylbicyclo[2.2.2]octane (17) ancillary groups significantly rescued iron-mediated oxidative stress in confluent PD-relevant SK-N-BE2-M17 neuroblastoma cells (M17 cells) exposed to 1,1'-dimethyl-4,4'-bipyridinium (paraquat, PQ) or H2O2. The second dose-dependence

  多巴胺能神经元的死亡是帕金森氏病（PD）的主要病理标志。PD脑黑质内的铁被认为可通过羟基自由基引起的氧化损伤来催化这种神经元死亡。去除这种过量的铁代表了PD的潜在治疗策略。通过金刚烷基-（1-4，8-12），解构的金刚烷基单元（5-7），降冰片（e）ne-（13- 16）或末端胺基的双环[2.2.2]辛烷基（17）辅助片段。实验logP值的范围为1-17（logP = 0.15-2.82）大于水溶性DFOB（logP -2.29），疏水性增加，旨在改善细胞膜的转运，促进细胞内铁的螯合。首次活性筛选显示，具有甲基取代的金刚烷基（1-3），去甲金刚烷基（5）或1-戊基双环[2.2.2]辛烷（17）辅助基团的化合物可在与PD相关的汇合性SK中显着缓解铁介导的氧化应激-N-BE2-M17神经母细胞瘤细胞（M17细胞）暴露于1,1'-二甲基-4,4'-联吡啶鎓（百草枯，PQ）或H2O2。在对PQ处理
• Discovery of Adamantane Carboxamides as Ebola Virus Cell Entry and Glycoprotein Inhibitors
  作者：Michael B. Plewe、Nadezda V. Sokolova、Vidyasagar Reddy Gantla、Eric R. Brown、Shibani Naik、Alexandra Fetsko、Donald D. Lorimer、David M. Dranow、Hayden Smutney、Jameson Bullen、Rana Sidhu、Arshil Master、Junru Wang、E. Adam Kallel、Lihong Zhang、Birte Kalveram、Alexander N. Freiberg、Greg Henkel、Ken McCormack

  DOI：10.1021/acsmedchemlett.0c00025

  日期：2020.6.11

  We identified and explored the structure–activity-relationship (SAR) of an adamantane carboxamide chemical series of Ebola virus (EBOV) inhibitors. Selected analogs exhibited half-maximal inhibitory concentrations (EC50 values) of ∼10–15 nM in vesicular stomatitis virus (VSV) pseudotyped EBOV (pEBOV) infectivity assays, low hundred nanomolar EC50 activity against wild type EBOV, aqueous solubility

  我们确定并探索了埃博拉病毒（EBOV）抑制剂的金刚烷羧酰胺化学系列的结构-活性关系（SAR）。选定的类似物在水疱性口炎病毒（VSV）假型EBOV（pEBOV）感染性试验中显示出约10–15 nM的半数最大抑制浓度（EC 50值），对野生型EBOV的低百纳摩尔EC 50活性，水溶性> 20 mg / mL，并且在人和非人肝微粒体中具有诱人的代谢稳定性。含EBOV糖蛋白（GP）的先导化合物的X射线共晶体表征确定EBOV GP为直接化合物抑制活性的靶标，并进一步提供了相关结构模型，可帮助鉴定优化的治疗候选物。
• 1-(Adamantyl) amidines and their use in the treatment of conditions generally associated with abnormalities in glutamatergic transmission
  申请人：VERNALIS RESEARCH LIMITED

  公开号：US20030130354A1

  公开（公告）日：2003-07-10

  Use of a compound of the formula (1), wherein X is an alkylene chain comprising 0, 1, 2, 3 or 4 carbon atoms; R 1 , R 2 and R 3 are independently selected from hydrogen, alkyl and aryl; R 4 , R 5 and R 6 are independently selected from hydrogen, alkyl, aryl, halogen and alkoxy; and prodrugs thereof and pharmaceutically acceptable salts thereof; in the manufacture of a medicament for use in the treatment of a condition generally associated with abnormalities in glutamatergic transmission.

  使用公式(1)中的化合物，其中X是一个碳原子数为0、1、2、3或4的烷基链；R1、R2和R3分别选择自氢、烷基和芳基；R4、R5和R6分别选择自氢、烷基、芳基、卤素和烷氧基；以及它们的前药和药物可接受的盐；用于制造治疗通常与谷氨酸能传递异常有关的疾病的药物。
• Oxadiazole Derivative as Dgat Inhibitors
  申请人：Birch Martin Alan

  公开号：US20080096874A1

  公开（公告）日：2008-04-24

  Compounds of formula (I), and salts and pro-drugs thereof: Formula (I) wherein for example R 1 is optionally substituted aryl or heteroaryl; Y is a linking group selected from, for example, a direct bond, and a (substituted) alkyl chain; R 2 is an optionally substituted aryl, an optionally substituted cycloalkyl or an optionally substituted heterocyclic group; are described. Processes to make such compounds and their use as DGAT inhibitors, for example in the treatment of obesity, are also described.

  式（I）的化合物，以及其盐和前药：其中，例如R1是可选取代芳基或杂环芳基；Y是选择自直接键和（取代）烷基链等的连接基；R2是可选取代芳基、可选取代环烷基或可选取代杂环基团。还描述了制备此类化合物的方法及其作为DGAT抑制剂的用途，例如在肥胖症的治疗中。
• OXADIAZOLE DERIVATIVES AS DGAT INHIBITORS
  申请人：BIRCH Alan Martin

  公开号：US20100317653A1

  公开（公告）日：2010-12-16

  Compounds of formula (I), and salts and pro-drugs thereof: wherein for example R 1 is optionally substituted aryl or heteroaryl; Y is a linking group selected from, for example, a direct bond, and a (substituted) alkyl chain; R 2 is an optionally substituted aryl, an optionally substituted cycloalkyl or an optionally substituted heterocyclic group; are described. Processes to make such compounds and their use as DGAT inhibitors, for example in the treatment of obesity, are also described.

  公式（I）的化合物、其盐和前药：其中，例如，R1是可选取代芳基或杂环芳基；Y是选自直接键和（取代）烷基链的连接基；R2是可选取代芳基、可选取代环烷基或可选取代杂环基团。本文描述了制备这种化合物的过程，以及它们作为DGAT抑制剂的用途，例如用于治疗肥胖症。