3-(环戊基氨基羰基)苯硼酸 | 850567-24-7

• 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-(环戊基氨基羰基)苯硼酸
• 中文别名: 3-(环戊基甲酰氨)苯基硼酸；3-(环戊基氨甲酰基)苯硼酸
• 英文名称: (3-(cyclopentylcarbamoyl)phenyl)boronic acid
• 英文别名: [3-(cyclopentylcarbamoyl)phenyl]boronic acid
• CAS: 850567-24-7
• 化学式: C₁₂H₁₆BNO₃
• mdl: MFCD04115695
• 分子量: 233.075
• InChiKey: KIOBFDGZJVJNBP-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-(Cyclopentylaminocarbonyl)phenylboronic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
3-(Cyclopentylaminocarbonyl)phenylboronic acid
Ingredient name:
CAS number: 850567-24-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H16BNO3
Molecular weight: 233.1

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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.

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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：

  3-(环戊基氨基羰基)苯硼酸 在 dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I) 、 碘苯二乙酸 、 silver(I) 4-methylbenzenesulfonate 作用下， 以 乙醚 、 1,1,2-三氯乙烷 为溶剂， 反应 10.0h， 生成 3'-(cyclopentylcarbamoyl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate
  参考文献：
  名称：

  金催化有机金属的氧化联芳基交叉偶联

  摘要：

  联芳基亲核试剂之间的偶联（AR δ-：arylboronates或芳基硅烷）和亲电（AR δ+：芳基卤化物）代表了碳-碳键形成的最新技术。这些反应中固有的官能团限制源于钯和镍催化剂对卤素，硼酸酯和碱敏感取代基的高催化反应性。在这里，我们报告了一般的二聚体金催化的芳基硼酸酯和芳基硅烷的氧化交叉偶联反应，而没有用于合成的外部碱，具有不对称联芳基的优异的官能团耐受性。两种偶合剂均易于获得，稳定且无毒。各种各样的（假）卤代和硼化偶合剂可以成功地应用于这种位点特定的联芳基偶合剂，具有前所未有的多功能性。简明地制备几种π共轭有机材料和药效基团已证实了其合成价值。

  DOI：

  10.1016/j.chempr.2019.07.023

文献信息

• Preparation and use of combustion derived Bi2O3 for the generation of novel heterocycles via Suzuki-Coupling Reactions: potential application as anti-cancer agents
  作者：Anusha Sebastian、Anandakumar B Siddappa、Chakrabhavi Dhananjaya Mohan、Nagabhushana G T、PRIYA BABU SHUBHA、Kanchugarakoppal S Rangappa、Salundi Basappa、Chandrappa G T

  DOI：10.1039/c4ra07839j

  日期：——

  Bismuth oxide was synthesized via simple, rapid and energy efficient solution combustion synthesis (SCS) by employing sucrose as a fuel. This SCS-Bi2O3 was characterized by analytical techniques such as PXRD, SEM, EDX, UV-Visible and BET surface area measurement. Using the prepared SCS-Bi2O3, several classes of heterocyclic compounds were synthesized in good yields via Suzuki-coupling reaction in aqueous medium. Interestingly, the recovered SCS-Bi2O3 could be reused three times without a significant loss of catalytic activity. Further, the synthesized compounds were tested for cytotoxic activity against a human hepatoma cancer cell line (HepG2). Among these, compound 3n effectively inhibited the proliferation of these cells with an IC50 value of 8.4 μM. Thus, this paper describes the preparation of highly effective Bi2O3, which can be used for synthesizing various classes of heterocycles, including those having anti-cancer property.

  铋氧化物通过简单、快速且能源高效的溶液燃烧合成（SCS）法合成，采用蔗糖作为燃料。所得到的SCS-Bi2O3通过PXRD、SEM、EDX、UV-可见光谱以及BET比表面积测量等分析技术进行了表征。利用制备的SCS-Bi2O3，通过在水相体系中进行铃木偶联反应合成了几类的杂环化合物，并且产率良好。有趣的是，回收的SCS-Bi2O3在没有显著失去催化活性的情况下可以重复使用三次。此外，合成的化合物还针对人肝癌细胞系（HepG2）进行了细胞毒性活性测试。其中，化合物3n有效抑制了这些细胞的增殖，IC50值为8.4 μM。因此，本文描述了高效的Bi2O3的制备，这可以用于合成包括具有抗癌特性的多种杂环化合物。
• Investigation of NPB Analogs That Target Phosphorylation of BAD-Ser99 in Human Mammary Carcinoma Cells
  作者：Swamy Savvemala Girimanchanaika、Dukanya Dukanya、Ananda Swamynayaka、Divya Maldepalli Govindachar、Mahendra Madegowda、Ganga Periyasamy、Kanchugarakoppal Subbegowda Rangappa、Vijay Pandey、Peter E. Lobie、Basappa Basappa

  DOI：10.3390/ijms222011002

  日期：——

  The loss of cell viability was enhanced by the NPB analogs synthesized by adding newer rings such as naphthalene and furan-2-carbaldehyde in place of N-cyclopentyl-benzamide of NPB. Furthermore, these compounds decreased Ser99 phosphorylation of hBAD. Additional in silico density functional theory calculations suggested possibilities for other analogs of NPB that may be more suitable for further development

  一种名为 NPB 的小分子 [3-(4(2,3-dichlorophenyl)piperazin-1-yl}2-hydroxyphenyl)methyl}-N-cyclopentylbenzamide] 的设计和开发，它在先前已报道过人类癌细胞中的 Ser99。本文报道了 NPB 类似物的合成、表征和对癌细胞活力的影响，以及通过缓慢溶剂蒸发技术生长的示例化合物 (4r) 的单晶 X 射线晶体学研究。对乳腺癌细胞活力丧失的筛查显示，诸如 2[(4(2,3-dichlorophenyl)piperazin-1-yl][naphthalen-1-yl]methyl)phenol (4e)、5[(4( 2,3-二氯苯基）哌嗪-1-基][2-羟基苯基）甲基）铀-2-甲醛（4f），3[（2-羟基苯基][4（对甲苯基）哌嗪-1-基）甲基）苯甲醛 (4i),50 个值分别为 5.90、3.11、7.68
• Design and Activity of Novel Oxadiazole Based Compounds That Target Poly(ADP-ribose) Polymerase
  作者：Divakar Vishwanath、Swamy S. Girimanchanaika、Dukanya Dukanya、Shobith Rangappa、Ji-Rui Yang、Vijay Pandey、Peter E. Lobie、Basappa Basappa

  DOI：10.3390/molecules27030703

  日期：——

  Novel PARP inhibitors with selective mode-of-action have been approved for clinical use. Herein, oxadiazole based ligands that are predicted to target PARP-1 have been synthesized and screened for the loss of cell viability in mammary carcinoma cells, wherein seven compounds were observed to possess significant IC50 values in the range of 1.4 to 25 µM. Furthermore, compound 5u, inhibited the viability of MCF-7 cells with an IC50 value of 1.4µM, when compared to Olaparib (IC50 = 3.2 µM). Compound 5s also decreased cell viability in MCF-7 and MDA-MB-231 cells with IC50 values of 15.3 and 19.2 µM, respectively. Treatment of MCF-7 cells with compounds 5u and 5s produced PARP cleavage, H2AX phosphorylation and CASPASE-3 activation comparable to that observed with Olaparib. Compounds 5u and 5s also decreased foci-formation and 3D Matrigel growth of MCF-7 cells equivalent to or greater than that observed with Olaparib. Finally, in silico analysis demonstrated binding of compound 5s towardsthe catalytic site of PARP-1, indicating that these novel oxadiazoles synthesized herein may serve as exemplars for the development of new therapeutics in cancer.

  新型选择性作用模式的PARP抑制剂已获批用于临床。在这里，预测能够靶向PARP-1的噁二唑基配体已经合成并在乳腺癌细胞中筛选，其中观察到七种化合物具有在1.4至25微米范围内的显著IC50值。此外，化合物5u抑制了MCF-7细胞的存活率，其IC50值为1.4微米，与Olaparib（IC50 = 3.2微米）相比。化合物5s也降低了MCF-7和MDA-MB-231细胞的存活率，分别为15.3和19.2微米。用化合物5u和5s处理MCF-7细胞产生了与Olaparib观察到的PARP裂解、H2AX磷酸化和CASPASE-3激活相当的效果。化合物5u和5s还降低了MCF-7细胞的聚焦形成和3D Matrigel生长，相当于或高于Olaparib观察到的效果。最后，计算机分析显示化合物5s结合到PARP-1的催化位点，表明这里合成的新型噁二唑可能作为癌症新疗法开发的示范物。
• Repurposing Human PDE4 Inhibitors for Neglected Tropical Diseases. Evaluation of Analogs of the Human PDE4 Inhibitor GSK-256066 as Inhibitors of PDEB1 of<i>Trypanosoma brucei</i>
  作者：Stefan O. Ochiana、Nicholas D. Bland、Luca Settimo、Robert K. Campbell、Michael P. Pollastri

  DOI：10.1111/cbdd.12443

  日期：2015.5

  Cyclic nucleotide phosphodiesterases (PDEs) have been identified as important enzyme targets for drug development in both humans and Trypanosoma brucei, the causative agent of human African trypanosomiasis. With this in mind, we recently reported the profiling of a range of human phosphodiesterase inhibitors, showing that human PDE4 inhibitors tend to display the best potency against the trypanosomal phosphodiesterase TbrPDEB1. Among these was GSK‐256066, a potent inhibitor of human PDE4 and a weak inhibitor of TbrPDEB1. In this report, we describe the results of a structure–activity relationship study of this chemotype, leading to the discovery of analogs with improved potency against TbrPDEB1 and micromolar inhibition of T. brucei cellular growth. We rationalize the potency trends via molecular docking of the new inhibitors into a recently reported apo structure of TbrPDEB1. The studies in this article will inform future efforts in repurposing human PDE inhibitors as antitrypanosomal agents.
• The synthesis and SAR of 2-amino-pyrrolo[2,3-d]pyrimidines: A new class of Aurora-A kinase inhibitors
  作者：Kevin J. Moriarty、Holly K. Koblish、Thomas Garrabrant、Jahanvi Maisuria、Ehab Khalil、Farah Ali、Ioanna P. Petrounia、Carl S. Crysler、Anna C. Maroney、Dana L. Johnson、Robert A. Galemmo

  DOI：10.1016/j.bmcl.2006.08.080

  日期：2006.11

  A new class of Aurora-A inhibitors have been identified based on the 2-amino-pyrrolo[2,3-d]pyrimidine scaffold. Here, we describe the synthesis and SAR of this novel series. We report compounds which exhibit nanomolar activity in the Aurora-A biochemical assay and are able to inhibit tumor cell proliferation. This study culminates in compound 30, an inhibitor with potent activity against Aurora A (IC50 = 0-008 mu M), anti-proliferative activity against several tumor cell lines and induces polyploidy in H460 cells. (c) 2006 Elsevier Ltd. All rights reserved.