4-(氨基羰基)-N-[(9H-芴-9-基甲氧基)羰基]-L-苯丙氨酸 | 204716-17-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-(氨基羰基)-N-[(9H-芴-9-基甲氧基)羰基]-L-苯丙氨酸
• 中文别名: (ALPHAS)-ALPHA-[[芴甲氧羰基]氨基]环戊烷乙酸；芴甲氧羰基-4-氨甲酰-L-苯丙氨酸
• 英文名称: N-Fmoc-L-4-Carbamoylphenylalanine
• 英文别名: Fmoc-L-4-carbamoyl phenylalanine；3-(4-carbamoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid；(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-carbamoylphenyl)propanoic acid；(2S)-3-(4-carbamoylphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 204716-17-6
• 化学式: C₂₅H₂₂N₂O₅
• 分子量: 430.46
• InChiKey: MUNGLNMRFZUOTD-QFIPXVFZSA-N

物化性质

• 沸点：
  713.4±60.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-L-4-carbamoylphe
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: Fmoc-L-4-carbamoylphe
CAS number: 204716-17-6

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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: C25H22N2O5
Molecular weight: 430.5

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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：

  4-(氨基羰基)-N-[(9H-芴-9-基甲氧基)羰基]-L-苯丙氨酸 在 哌啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 为溶剂， 生成 4-{(S)-2-Amino-3-oxo-3-[(S)-3-(4-phenyl-1H-imidazol-2-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-propyl}-benzamide
  参考文献：
  名称：

  Identification of potent phenyl imidazoles as opioid receptor agonists

  摘要：

  Using previously reported opioid receptor (OR) agonist analogs 4a-c as starting points, the structure-activity relationship (SAR) for their related series has been further refined. This SAR Study has led to the identification of 2,6-di-Me-Tyr (DMT) analogs 4h and 4j as the most potent OR agonist within the series. in addition, it was discovered that 4-(aminocarbonyl)-2,6-dimethyl-Phe is a reasonable bioisostere surrogate for the DMT moiety, as supported by the OR activities Of Compounds 4x and 4y. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.082
• 作为产物：
  描述：

  L-Phenylalanine, 4-carboxy-N-[(phenylmethoxy)carbonyl]-, I+/--(phenylmethyl) ester 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 sodium carbonate 、 氯化铵 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 4-(氨基羰基)-N-[(9H-芴-9-基甲氧基)羰基]-L-苯丙氨酸
  参考文献：
  名称：

  制备伯酰胺的一种选择性方法：Fmoc-1-4-羧酰胺基苯丙氨酸和其他化合物的合成

  摘要：

  开发了一种新的合成伯酰胺的方法，其中在肽合成偶联剂和碱存在下，在室温下用氯化铵处理羧酸。这些温和的条件使羧基能够在具有敏感官能团（例如酯和对碱不稳定的Fmoc保护基）的底物上转化为伯酰胺。

  DOI：

  10.1016/s0040-4039(99)00245-2

文献信息

• Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor
  作者：Kaicheng Meng、Paul Shim、Qingtin Wang、Shuai Zhao、Ting Gu、Alem W. Kahsai、Seungkirl Ahn、Xin Chen

  DOI：10.1016/j.bmc.2018.03.023

  日期：2018.5

  The β2-adrenergic receptor (β2AR), a G protein-coupled receptor, is an important therapeutic target. We recently described Cmpd-15, the first small molecule negative allosteric modulator (NAM) for the β2AR. Herein we report in details the design, synthesis and structure-activity relationships (SAR) of seven Cmpd-15 derivatives. Furthermore, we provide in a dose-response paradigm, the details of the

  所述β 2 -肾上腺素能受体（β 2 AR），G蛋白偶联受体，是一个重要的治疗目标。我们最近描述CMPD-15，第一小分子负变构调节剂（NAM）为β 2 AR。本文中，我们详细报告了7种CMPD-15衍生物的设计，合成和构效关系（SAR）。此外，我们提供一种在剂量-响应范例，它们的衍生物的效果的细节在调节激动剂诱导的β 2在放射性配体竞争结合试验中，AR活性（G蛋白介导的cAMP产生和β-arrestin募集到受体）以及正构激动剂的结合亲和力。我们的研究结果表明，一些修改，包括在除去甲酰胺基的第-formAMido苯丙氨酸区域和溴在元-bromobenzyl甲基苯甲酰胺区域引起CMPD-15的功能活性显着降低。这些SAR结果提供了宝贵的见解NAM CMPD-15的作用机制以及为更有效和选择性调节剂的未来发展，为β的基础2基于CMPD-15的化学支架AR。
• Novel compounds as opioid receptor modulators
  申请人：——

  公开号：US20040010014A1

  公开（公告）日：2004-01-15

  This invention is directed towards novel compounds as opioid receptor modulators, antagonists, and agonists useful for the treatment of opioid modulated disorders such as pain and gastrointestinal disorders.

  这项发明针对的是作为阿片受体调节剂、拮抗剂和激动剂的新型化合物，它们可用于治疗由阿片类药物调节的疾病，如疼痛和胃肠疾病。
• [EN] HETEROCYCLIC DERIVATIVES AS IAP BINDING COMPOUNDS<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES CONVENANT COMME COMPOSÉS SE LIANT AUX INHIBITEURS DE PROTÉINES D'APOPTOSE
  申请人：NUEVOLUTION AS

  公开号：WO2009152824A1

  公开（公告）日：2009-12-23

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, solvates thereof, that bind to Inhibitor of Apoptosis Proteins (IAPs). The compounds of the invention may be used as diagnostic and therapeutic agents in the treatment of proliferative diseases, such as cancer, for promoting apoptosis in proliferating cells, and for sensitizing cells to inducers of apoptosis. The present invention furthermore provides a polymeric compound of formulas (VI) or (VII), comprising either at least two monomeric units of compounds of formula (I), or at least one monomeric unit of a compound of formula (I) and an entity E. The present invention further relates to pharmaceutical compositions comprising said compounds of formulas (I), (VI), and (VII) and the use of said compounds in medicine.

  本发明涉及式(I)的化合物，或其药学上可接受的盐、溶剂化合物，这些化合物与凋亡抑制蛋白(IAPs)结合。本发明的化合物可用作诊断和治疗剂，用于治疗增殖性疾病，如癌症，促进增殖细胞中的凋亡，并使细胞对凋亡诱导剂敏感。本发明还提供了具有式(VI)或(VII)的聚合物化合物，包括至少两个式(I)化合物的单体单位，或至少一个式(I)化合物的单体单位和实体E。本发明还涉及包含所述式(I)、(VI)和(VII)化合物的药物组合物以及在医学中使用所述化合物的用途。
• SAR evolution towards potent C-terminal carboxamide peptide inhibitors of Zika virus NS2B-NS3 protease
  作者：Stefania Colarusso、Federica Ferrigno、Simona Ponzi、Francesca Pavone、Immacolata Conte、Luigi Abate、Elisa Beghetto、Antonino Missineo、Jerome Amaudrut、Alberto Bresciani、Giacomo Paonessa、Licia Tomei、Christian Montalbetti、Elisabetta Bianchi、Carlo Toniatti、Jesus M. Ontoria

  DOI：10.1016/j.bmc.2022.116631

  日期：2022.3

  Zika virus (ZIKV) is a member of the Flaviviridae family that can cause neurological disorders and congenital malformations. The NS2B-NS3 viral serine protease is an attractive target for the development of new antiviral agents against ZIKV. We report here a SAR study on a series of substrate-like linear tripeptides that inhibit in a non-covalent manner the NS2B-NS3 protease. Optimization of the residues

  寨卡病毒 (ZIKV) 是黄病毒科的成员，可导致神经系统疾病和先天性畸形。NS2B-NS3 病毒丝氨酸蛋白酶是开发针对 ZIKV 的新抗病毒药物的有吸引力的目标。我们在此报告了对以非共价方式抑制 NS2B- 蛋白酶的一系列底物样线性三肽的 SAR 研究。优化位置P 1、P 2、P 3 和N的残基三肽的-末端和C-末端部分允许鉴定具有亚微摩尔效力的抑制剂，其中苯基甘氨酸作为精氨酸模拟基团和苯甲酰胺作为C-末端片段。进一步的 SAR 探索和将这些结构变化应用于在P 1 位具有 4 个取代的苯基甘氨酸残基的一系列肽，导致有效的化合物显示出对寨卡蛋白酶 (IC 50  = 30 nM) 具有高选择性的两位数纳摩尔抑制作用胰蛋白酶样蛋白酶和其他黄病毒的蛋白酶，例如登革热 2 病毒 (DEN2V) 和西尼罗河病毒 (WNV)。
• Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts
  作者：Lei Jin、Shuai Zhao、Xin Chen

  DOI：10.3390/molecules23061421

  日期：——

  A practical synthesis of both enantiomers of unnatural phenylalanine derivatives by using two pseudoenantiomeric phase transfer catalysts is described. Through asymmetric α-alkylation of glycine Schiff base with substituted benzyl bromides and 1-(bromomethyl)naphthalene under the catalysis of O-allyl-N-(9-anthracenmethyl) cinchoninium bromide (1f) and O-allyl-N-(9-anthracenylmethyl)cinchonidium bromide

  描述了使用两种假对映体相转移催化剂来实际合成非天然苯丙氨酸衍生物的两种对映体。在O-烯丙基-N-(9-蒽甲基)辛可宁溴化物(1f)和O-烯丙基-N-(9-)催化下，甘氨酸席夫碱与取代的苄基溴和1-(溴甲基)萘发生不对称α-烷基化反应分别以优异的产率和对映选择性获得了一系列非天然α-氨基酸衍生物的(R)-和(S)-对映体。该合成方法简单、可规模化，产物的立体化学完全可预测和控制：辛可宁型相转移催化剂1f得到(R)-α-氨基酸衍生物，辛可尼定型相转移催化剂1i得到(R)-α-氨基酸衍生物。 (S)-α-氨基酸衍生物。