4-(1-羧基环丙基)苯硼酸 | 1159489-46-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 4-(1-羧基环丙基)苯硼酸
• 中文别名: 4-(1-羧基环丙基)苯基硼酸
• 英文名称: [4-(1'-carboxycyclopropyl)phenyl]boronic acid
• 英文别名: 1-[4-(dihydroxyboryl)phenyl]cyclopropanecarboxylic acid；4-(1'-carboxyl-cyclopropyl)phenylboronic acid；1-(4-boronophenyl)cyclopropanecarboxylic acid；1-(4-boronophenyl)cyclopropane-1-carboxylic acid
• CAS: 1159489-46-9
• 化学式: C₁₀H₁₁BO₄
• 分子量: 206.006
• InChiKey: PUBSPRJVEBBDPX-UHFFFAOYSA-N

物化性质

• 沸点：
  445.1±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.52
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(1-Carboxycyclopropyl)phenylboronic acid
Synonyms: 1-(4-Boronophenyl)cyclopropanecarboxylic acid

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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: 4-(1-Carboxycyclopropyl)phenylboronic acid
CAS number: 1159489-46-9

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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: C10H11BO4
Molecular weight: 206.0

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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.

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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-(1-羧基环丙基)苯硼酸 在 potassium phosphate 、 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 硫酸 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 1-{4'-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester
  参考文献：
  名称：

  通过串联硼基化-铃木法开发LPA-1拮抗剂BMS-986020的简明多千克合成方法

  摘要：

  描述了通过钯催化的串联硼酸化/ Suzuki反应合成BMS-986020（1）的方法。在四步中，使用四羟基二硼进行有效的硼酸酯化步骤，然后进行串联的铃木反应，使用有效的钯化催化剂进行条件评估。该方法论解决了早期合成路线的缺点，并最终用于活性药物成分1的多公斤级合成。对该硼化反应的进一步评估显示出与一系列取代的芳基溴化物和碘化物作为偶联伙伴的有用的反应性。这些发现代表了一种实用，有效，温和且可扩展的硼酸化方法。

  DOI：

  10.1021/acs.oprd.7b00301
• 作为产物：
  描述：

  1-(4-溴苯基)环丙甲酸 生成 4-(1-羧基环丙基)苯硼酸
  参考文献：
  名称：

  Org. Process Res. Dev. 2017, 21, 1859-1863

  摘要：

  DOI：

文献信息

• C-3 benzoic acid derivatives of C-3 deoxybetulinic acid and deoxybetulin as HIV-1 maturation inhibitors
  作者：Zheng Liu、Jacob J. Swidorski、Beata Nowicka-Sans、Brian Terry、Tricia Protack、Zeyu Lin、Himadri Samanta、Sharon Zhang、Zhufang Li、Dawn D. Parker、Sandhya Rahematpura、Susan Jenkins、Brett R. Beno、Mark Krystal、Nicholas A. Meanwell、Ira B. Dicker、Alicia Regueiro-Ren

  DOI：10.1016/j.bmc.2016.03.001

  日期：2016.4

  A series of C-3 phenyl- and heterocycle-substituted derivatives of C-3 deoxybetulinic acid and C-3 deoxybetulin was designed and synthesized as HIV-1 maturation inhibitors (MIs) and evaluated for their antiviral activity and cytotoxicity in cell culture. A 4-subsituted benzoic acid moiety was identified as an advantageous replacement for the 3′3′-dimethylsuccinate moiety present in previously disclosed

  设计并合成了一系列C-3脱氧贝丁酸和C-3脱氧贝丁酸的C-3苯基和杂环取代衍生物，作为HIV-1成熟抑制剂（MIs），并评估了它们在细胞培养中的抗病毒活性和细胞毒性。鉴定出4-取代的苯甲酸部分是先前公开的MI中存在的3'3'-二甲基琥珀酸酯部分的有利替代物，其阐明了药效团的拓扑学的新方面。与原型HIV-1 MI bevirimat（1，BVM）相比，新的类似物对野生型（wt）病毒具有出色的体外抗病毒活性，并且血清转移降低，这是临床研究中第一个评估的MI。化合物9a对wt病毒表现出与1类似的细胞培养能力（ 对于9a， WT EC 50 = 16 nM，而对于1a，则为10 nM ）。但是，9a的效力受人血清的影响较小，而该化合物在大鼠中的药代动力学特征与1相似。因此，9a（脱氧贝丁酸的4-苯甲酸衍生物）代表了探索第二代MI设计的新起点。
• [EN] COMPOSITIONS AND METHODS FOR MODULATING LPA RECEPTORS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LA MODULATION DE RÉCEPTEURS AU LPA
  申请人：IRM LLC

  公开号：WO2012138648A1

  公开（公告）日：2012-10-11

  The present invention relates to compounds of Formula (1), or pharmaceutically acceptable salts thereof and their pharmaceutical compositions, wherein variables are as defined herein, which are useful as modulators of the activity of lysophosphatidic acid (LPA).

  本发明涉及式（1）的化合物或其药用盐及其药物组合物，其中变量如本文所定义，这些化合物可用作溶血磷脂酸（LPA）活性的调节剂。
• [EN] CYSTEINE PROTEASE INHIBITORS FOR THE TREATMENT OF PARASITIC DISEASES<br/>[FR] INHIBITEURS DE CYSTÉINE-PROTÉASES POUR LE TRAITEMENT DE MALADIES PARASITAIRES
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2009067797A1

  公开（公告）日：2009-06-04

  Several parasites responsible for mammalian diseases are dependent on cysteine protease for various life-cycle functions. Inhibition or decreasing function of these proteases can be useful in the treatment and/or prevention of these parasitic diseases including; toxoplasmosis, malaria, African trypanosomiasis, Chagas disease, leishmaniasis, schistosomiasis, amebiasis, giardiasis, clonorchiasis, opisthorchiasis, paragonimiasis, fasciolopsiasis, lymphatic filariasis, onchocerciasis, dracunculiasis, ascariasis, trichuriasis, strongyloidiasis, trichostrongyliasis, trichomoniasis or cestodiasis. Compounds of formula I of the invention are capable of treating and/or preventing the above-identified diseases:

  一些导致哺乳动物疾病的寄生虫依赖半胱氨酸蛋白酶进行各种生命周期功能。抑制或减少这些蛋白酶的功能可以在治疗和/或预防包括弓形虫病、疟疾、非洲锥虫病、克氏病、利什曼病、血吸虫病、阿米巴病、贾第虫病、华支睾吸虫病、华支睾吸虫病、肺吸虫病、淋巴丝虫病、显微丝虫病、蛔虫病、鞭虫病、强力虫病、毛圆线虫病、滴虫病或绦虫病等寄生虫病方面发挥作用。本发明的I类化合物能够治疗和/或预防上述疾病。
• Discovery of Potent and Selective 7-Azaindole Isoindolinone-Based PI3Kγ Inhibitors
  作者：Dillon H. Miles、Xuelei Yan、Rhiannon Thomas-Tran、Jeremy Fournier、Ehesan U. Sharif、Samuel L. Drew、Guillaume Mata、Kenneth V. Lawson、Elaine Ginn、Kent Wong、Divyank Soni、Puja Dhanota、Stefan G. Shaqfeh、Cesar Meleza、Ada Chen、Amber T. Pham、Timothy Park、Debbie Swinarski、Jesus Banuelos、Ulrike Schindler、Matthew J. Walters、Nigel P. Walker、Xiaoning Zhao、Stephen W. Young、Jie Chen、Lixia Jin、Manmohan Reddy Leleti、Jay P. Powers、Jenna L. Jeffrey

  DOI：10.1021/acsmedchemlett.0c00387

  日期：2020.11.12

  The successful application of immunotherapy in the treatment of cancer relies on effective engagement of immune cells in the tumor microenvironment. Phosphoinositide 3-kinase γ (PI3Kγ) is highly expressed in tumor-associated macrophages, and its expression levels are associated with tumor immunosuppression and growth. Selective inhibition of PI3Kγ offers a promising strategy in immuno-oncology, which

  免疫疗法在癌症治疗中的成功应用依赖于免疫细胞在肿瘤微环境中的有效参与。磷酸肌醇 3-激酶γ（PI3Kγ）在肿瘤相关巨噬细胞中高表达，其表达水平与肿瘤免疫抑制和生长有关。PI3Kγ 的选择性抑制为免疫肿瘤学提供了一种有前景的策略，这导致开发了许多具有可变选择性特征的有效 PI3Kγ 抑制剂。为了促进对 PI3Kγ 抑制的治疗潜力的进一步研究，我们需要一种有效的 PI3Kγ 选择性工具化合物，具有足够的代谢稳定性，以供将来在体内使用学习。在此，我们描述了我们通过系统研究一系列基于 7-氮杂吲哚的 PI3Kγ 抑制剂中的 SAR 来实现这一目标的一些努力。本研究产生的大量数据有助于指导我们随后的先导优化工作，并将为用于免疫调节的 PI3Kγ 选择性抑制剂的进一步开发提供信息。
• [EN] POLYCYCLIC LPA1 ANTAGONIST AND USES THEREOF<br/>[FR] ANTAGONISTE LPA1 POLYCYCLIQUE ET UTILISATIONS DE CELUI-CI
  申请人：AMIRA PHARMACEUTICALS INC

  公开号：WO2012078805A1

  公开（公告）日：2012-06-14

  Described herein is the LPA1 antagonist 1- 4'-[3-methyl-4-((R)- l-phenyl-ethoxycarbonylamino)- isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid (Compound 1), or pharmaceutically acceptable salts thereof. Also described are methods of preparing the LPA1 antagonist, or pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions suitable for administration to a mammal that include the LPA1 antagonist, or pharmaceutically acceptable salt thereof, and methods of using such pharmaceutical compositions for treating LPA-dependent or LPA- mediated diseases or conditions.

  本文描述了LPA1拮抗剂1-4'-[3-甲基-4-((R)- l-苯基-乙氧羰基氨基)-异噁唑-5-基]-联苯基-4-基}-环丙烷羧酸（化合物1），或其药用盐。还描述了制备LPA1拮抗剂或其药用盐的方法，以及适用于哺乳动物的药物组合物，包括LPA1拮抗剂或其药用盐，并且使用这种药物组合物治疗依赖于LPA或LPA介导的疾病或病症的方法。