3-(2H-四唑-5-基)-苯硼酸 | 775351-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(2H-四唑-5-基)-苯硼酸
• 中文别名: 3-(1H-四唑-5-基)苯硼酸
• 英文名称: (3-(1H-tetrazol-5-yl)phenyl)boronic acid
• 英文别名: 3-(Tetrazol-5-YL)phenylboronic acid；[3-(2H-tetrazol-5-yl)phenyl]boronic acid
• CAS: 775351-30-9
• 化学式: C₇H₇BN₄O₂
• mdl: MFCD06739100
• 分子量: 189.969
• InChiKey: XMJKBDSKRITXBW-UHFFFAOYSA-N

物化性质

• 沸点：
  517.4±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-(2H-Tetrazol-5-yl)-phenyl-boronic acid
Synonyms: 3-(Tetrazol-5-yl)phenylboronic acid

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-(2H-Tetrazol-5-yl)-phenyl-boronic acid
CAS number: 775351-30-9

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C7H7BN4O2
Molecular weight: 190.0

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(2H-四唑-5-基)-苯硼酸 在 sodium tetrahydroborate 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.08h， 生成
  参考文献：
  名称：

  新型强效二肽基肽酶4抑制剂的设计，合成和SAR研究

  摘要：

  二肽基肽酶4（DPP-4）是经临床验证的2型糖尿病（T2DM）治疗靶标。发现新的和有效的DPP-4抑制剂，三个系列化合物的基于我们先前鉴定的新型支架设计并合成在这项研究中的2-苯基-3,4-二氢-2 ħ -苯并[ ˚F ]苯并吡喃-3-胺。在设计的化合物中，41d-1是最有效的化合物，IC 50值为16.00 nM。此外，ICR小鼠的41d-1（5 mg / kg）表现出中等的葡萄糖耐量。详细讨论了结构活动关系（SAR）研究，这对我们的进一步优化具有建设性。

  DOI：

  10.1002/cjoc.202000342
• 作为产物：
  描述：

  3-氰基苯硼酸 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以15%的产率得到3-(2H-四唑-5-基)-苯硼酸
  参考文献：
  名称：

  WO2008/23161

  摘要：

  公开号：
• 作为试剂：
  描述：

  3-(2H-四唑-5-基)-苯硼酸 、 2-溴-6-硝基苯酚 在 3-(2H-四唑-5-基)-苯硼酸 作用下， 生成 3-nitro-3'-(1H-tetrazol-5-yl)-2-biphenylol
  参考文献：
  名称：

  2-(3,4-dimethylphenyl)-4-{[2-hydroxy-3′-(1h-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one choline

  摘要：

  一种改进的血小板生成素类似物，即2-(3,4-二甲基苯基)-4-{[2-羟基-3′-(1H-四唑-5-基)联苯-3-基]-肼基}-5-甲基-2，4-二氢吡唑-3-酮的胆碱盐。

  公开号：

  US07666857B2

文献信息

• [EN] TRIAZOLONE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE TRIAZOLONE ET LEURS UTILISATIONS
  申请人：INCEPTION 2 INC

  公开号：WO2013134562A1

  公开（公告）日：2013-09-12

  The invention disclosed herein is directed to compounds of Formula (I) and pharmaceutically acceptable salts thereof, which are useful in the treatment of prostate, breast, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention also comprises pharmaceutical compositions comprising a therapeutically effective amount of compound of Formula (I), or a pharmaceutically acceptable salt thereof. The invention disclosed herein is also directed to methods of treating prostate, breast, ovarian, liver, kidney, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention disclosed herein is further directed to methods of treating prostate, breast, colon, pancreatic, chronic lymphocytic leukemia, melanoma and other cancers comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist. The compounds and pharmaceutical compositions of the invention are also useful in the treatment of viral infections, such as HCV infections and HIV infections. The invention disclosed herein is also directed to a methods of preventing the onset of and/or recurrence of acute and chronic myeloid leukemia, as well as other cancers, comprising administration of a of a therapeutically effective amount of a selective PPARα antagonist.

  本发明涉及的化合物属于式(I)及其药学上可接受的盐，可用于治疗前列腺、乳腺、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症。该发明还包括含有式(I)化合物的治疗有效量或其药学上可接受的盐的药物组合物。本发明还涉及治疗前列腺、乳腺、卵巢、肝脏、肾脏、结肠、胰腺、人类慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法。本发明还涉及治疗前列腺、乳腺、结肠、胰腺、慢性淋巴细胞白血病、黑色素瘤和其他癌症的方法，包括给予选择性PPARα拮抗剂的治疗有效量。本发明的化合物和药物组合物还可用于治疗病毒感染，如HCV感染和HIV感染。本发明还涉及一种预防急性和慢性骨髓性白血病以及其他癌症发作和/或复发的方法，包括给予选择性PPARα拮抗剂的治疗有效量。
• 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] FATTY ACID SYNTHASE INHIBITORS<br/>[FR] INHIBITEURS DE L'ACIDE GRAS SYNTHASE
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2012037298A1

  公开（公告）日：2012-03-22

  This invention relates to the use of imidazole, triazole, and tetrazole derivatives for the modulation, notably the inhibition of the activity or function of fatty acid synthase (FAS). Suitably, the present invention relates to the use of imidazoles, triazoles, and tetrazoles in the treatment of cancer.

  这项发明涉及使用咪唑、三唑和四唑衍生物来调节，尤其是抑制脂肪酸合酶（FAS）的活性或功能。适当地，本发明涉及在癌症治疗中使用咪唑、三唑和四唑。
• Discovery of potent and selective orally bioavailable β-substituted phenylalanine derived dipeptidyl peptidase IV inhibitors
  作者：Scott D. Edmondson、Anthony Mastracchio、Joseph L. Duffy、George J. Eiermann、Huaibing He、Ida Ita、Barbara Leiting、Joseph F. Leone、Kathryn A. Lyons、Amanda M. Makarewicz、Reshma A. Patel、Aleksandr Petrov、Joseph K. Wu、Nancy A. Thornberry、Ann E. Weber

  DOI：10.1016/j.bmcl.2005.04.028

  日期：2005.6

  nine derived amides have been shown to be potent DPP-IV inhibitors that suffer from suboptimal selectivity and pharmacokinetics. This letter describes the substitution of the beta-methyl substituent with beta-polar substituents, culminating in the discovery of a beta-dimethylamide substituted phenylalanine derivative with an excellent potency, selectivity, and pharmacokinetic profile.

  抗取代的联芳基β-甲基苯基丙氨酸衍生的酰胺已被证明是有效的DPP-IV抑制剂，其选择性和药物动力学都不理想。这封信描述了用β-极性取代基取代β-甲基取代基，最终发现了具有出色效价，选择性和药代动力学特征的β-二甲基酰胺取代的苯丙氨酸衍生物。
• SAR Exploration of Tight-Binding Inhibitors of Influenza Virus PA Endonuclease
  作者：Cy V. Credille、Christine N. Morrison、Ryjul W. Stokes、Benjamin L. Dick、Yifan Feng、Jiaxing Sun、Yao Chen、Seth M. Cohen

  DOI：10.1021/acs.jmedchem.9b00747

  日期：2019.11.14

  relationships were established and used to generate inhibitors of influenza endonuclease with tight-binding affinities. The activity of these inhibitors was analyzed using a fluorescence-quenching-based nuclease activity assay, and binding was validated using differential scanning fluorometry. Lead compounds were found to be highly selective for PAN endonuclease against several related dinuclear and mononuclear

  据报道，在流感抗病毒药的开发方面做出了重大努力，包括RNA依赖性RNA聚合酶PA N端（PAN）核酸内切酶抑制剂。基于最近鉴定出的用于抑制PAN核酸内切酶的高活性金属结合药效基团（MBP），开展了基于片段的药物开发活动。在配位化学和基于结构的药物设计的指导下，MBP支架被精制以提高活性和选择性。建立了结构-活性关系并用于产生具有紧密结合亲和力的流感核酸内切酶抑制剂。使用基于荧光猝灭的核酸酶活性测定法分析这些抑制剂的活性，并使用差示扫描荧光法验证结合。发现铅化合物对PAN核酸内切酶对几种相关的双核和单核金属酶具有高度选择性。这项研究中结合了生物无机和药物化学原理，产生了一些具有高配体效率的最活跃的体外流感PAN核酸内切酶抑制剂。