Fmoc-l-吲哚啉-2-羧酸 | 198560-38-2

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-l-吲哚啉-2-羧酸
• 中文别名: FMOC-L-二氢吲哚-2-甲羧酸；Fmoc-L-二氢吲哚-2-羧酸
• 英文名称: Fmoc-l-indoline-2-carboxylic acid
• 英文别名: (2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-2,3-dihydroindole-2-carboxylic acid
• CAS: 198560-38-2
• 化学式: C₂₄H₁₉NO₄
• 分子量: 385.419
• InChiKey: FWYAYXBFHLDIRA-QFIPXVFZSA-N

物化性质

• 沸点：
  609.8±54.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 储存条件：
  存储温度应保持在0°C。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-L-Indoline-2-carboxylic acid
Synonyms: Fmoc-L-IDC-OH

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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: Fmoc-L-Indoline-2-carboxylic acid
CAS number: 198560-38-2

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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.
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: C24H19NO4
Molecular weight: 385.4

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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.

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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：

  Fmoc-l-吲哚啉-2-羧酸 在 2,4,6-三甲基吡啶 、 磷酸 、 palladium 10% on activated carbon 、 氢气 、 二乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 (S)-6-(((S)-1-((S)-1-(((S)-2-carboxy-1-cyanoethyl)carbamoyl)-6-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-3-methyl-1-oxobutan-2-yl)amino)-5-((S)-indoline-2-carboxamido)-6-oxohexanoic acid
  参考文献：
  名称：

  Caspase-2 抑制剂阻断 Tau 截断并恢复神经元中的兴奋性神经传递 FTDP-17 Tauopathy 建模

  摘要：

  由树突棘中神经元蛋白 tau 的不成比例积累引起的兴奋性神经传递严重减少介导的突触和认知缺陷是一种基本机制，在 tau 病变模型中反复发现，包括阿尔茨海默病、路易体痴呆、额颞叶痴呆、和外伤性脑损伤。如此受损的突触可能会导致痴呆症，这是导致老年人虚弱的最可怕的原因之一，目前还没有修复它们的治疗方法。Caspase-2 (Casp2) 是这种病理级联反应的重要组成部分。虽然据信 Casp2 通过在天冬氨酸 314 处水解 tau 来发挥其作用，形成 Δtau314，也可能涉及非催化机制，因为催化死亡的 Casp2 在至少一种相关的细胞途径（即自噬）中具有生物活性。为了破译 Casp2 对突触功能的病理影响是否是由于其催化或非催化特性，我们发现并表征了一种新的 Casp2 抑制剂，化合物1 [p K i (Casp2) = 8.12]，其选择性比 Casp3 高 123 倍，比 Casp1、Casp6、Casp7

  DOI：

  10.1021/acschemneuro.2c00100

文献信息

• 6,5‐Fused Ring, C2‐Salvinorin Ester, Dual Kappa and Mu Opioid Receptor Agonists as Analgesics Devoid of Anxiogenic Effects**
  作者：Nicholas S. Akins、Nisha Mishra、Hannah M. Harris、Narendar Dudhipala、Seong Jong Kim、Adam W. Keasling、Soumyajit Majumdar、Jordan K. Zjawiony、Jason J. Paris、Nicole M. Ashpole、Hoang V. Le

  DOI：10.1002/cmdc.202100684

  日期：2022.4.5

  Salvinorin-based Analgesics: Compounds with dual agonism to opioid receptor subtypes have been suggested to reduce adverse effects while retaining analgesic activity. Herein we report the introduction of various 6,5-fused rings to C2 of the salvinorin scaffold via an ester linker. The lead dual kappa and mu opioid receptor agonist demonstrated supraspinal thermal analgesic activity while avoiding anxiogenic

  基于 Salvinorin 的镇痛药：已建议对阿片受体亚型具有双重激动作用的化合物可减少不良反应，同时保持镇痛活性。在此，我们报告了通过酯连接体将各种 6,5-稠合环引入 salvinorin 支架的 C2 。先导双重 kappa 和 mu 阿片受体激动剂在雄性小鼠中表现出脊髓上热镇痛活性，同时避免产生焦虑作用。
• Novel Ergopeptides as Dual Ligands for Adenosine and Dopamine Receptors
  作者：Marc Vendrell、Ester Angulo、Vicent Casadó、Carme Lluis、Rafael Franco、Fernando Albericio、Miriam Royo

  DOI：10.1021/jm060947x

  日期：2007.6.1

  prepared dual ligands acting on adenosine and dopamine receptors by applying a combinatorial approach based on the ergolene privileged structure. The potency and efficacy of these novel compounds were determined by radioligand binding studies and intracellular cAMP production assays in cells expressing adenosine and dopamine receptors. Selected compounds displayed dual dopamine agonist and adenosine

  多价配体是有前途的药理学工具，对多种疾病的治疗可能比高度选择性的单靶标药物更为有效。目前正在评估使用多巴胺能激动剂和腺苷能拮抗剂的联合疗法，以治疗帕金森氏病。[（a）Kanda，T .; 等。经验值 神经元。2000、162、321-327。（b）詹纳，体育专家。投资。药物，2005，14，729-738。（c）Kase，H .；等。Neurology 2003，61（Suppl 6），S97-S100。]在这里，我们通过基于麦角蛋白优先结构的组合方法制备了作用于腺苷和多巴胺受体的双重配体。这些新化合物的效力和功效通过放射性配体结合研究和表达腺苷和多巴胺受体的细胞内细胞内cAMP产生测定来确定。选定的化合物表现出双重多巴胺激动剂和腺苷拮抗剂活性。具有这种药理学特征的分子对于研究中枢神经系统中的多巴胺-腺苷串扰以及测试多价药物对帕金森氏病的治疗潜力具有潜在的实用性。
• EP4112631
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2023/164238
  申请人：——

  公开号：——

  公开（公告）日：——
• Caspase-2 Inhibitor Blocks Tau Truncation and Restores Excitatory Neurotransmission in Neurons Modeling FTDP-17 Tauopathy
  作者：Gurpreet Singh、Peng Liu、Katherine R. Yao、Jessica M. Strasser、Chris Hlynialuk、Kailee Leinonen-Wright、Peter J. Teravskis、Jessica M. Choquette、Junaid Ikramuddin、Merlin Bresinsky、Kathryn M. Nelson、Dezhi Liao、Karen H. Ashe、Michael A. Walters、Steffen Pockes

  DOI：10.1021/acschemneuro.2c00100

  日期：2022.5.18

  cognitive deficits mediated by a severe reduction in excitatory neurotransmission caused by a disproportionate accumulation of the neuronal protein tau in dendritic spines is a fundamental mechanism that has been found repeatedly in models of tauopathies, including Alzheimer’s disease, Lewy body dementia, frontotemporal dementia, and traumatic brain injury. Synapses thus damaged may contribute to dementia

  由树突棘中神经元蛋白 tau 的不成比例积累引起的兴奋性神经传递严重减少介导的突触和认知缺陷是一种基本机制，在 tau 病变模型中反复发现，包括阿尔茨海默病、路易体痴呆、额颞叶痴呆、和外伤性脑损伤。如此受损的突触可能会导致痴呆症，这是导致老年人虚弱的最可怕的原因之一，目前还没有修复它们的治疗方法。Caspase-2 (Casp2) 是这种病理级联反应的重要组成部分。虽然据信 Casp2 通过在天冬氨酸 314 处水解 tau 来发挥其作用，形成 Δtau314，也可能涉及非催化机制，因为催化死亡的 Casp2 在至少一种相关的细胞途径（即自噬）中具有生物活性。为了破译 Casp2 对突触功能的病理影响是否是由于其催化或非催化特性，我们发现并表征了一种新的 Casp2 抑制剂，化合物1 [p K i (Casp2) = 8.12]，其选择性比 Casp3 高 123 倍，比 Casp1、Casp6、Casp7