4-硝基联苯-3-羧酸 | 729-01-1

• 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-硝基联苯-3-羧酸
• 英文名称: 4'-nitrobiphenyl-3-carboxylic acid
• 英文别名: 4'-nitro-[1,1'-biphenyl]-3-carboxylic acid；4-nitro-3'-carboxylbiphenyl；4-nitro-3'-carboxybiphenyl；4'-nitro-biphenyl-3-carboxylic acid；4'-Nitro-biphenyl-3-carbonsaeure；3-(4-nitrophenyl)benzoic acid
• CAS: 729-01-1
• 化学式: C₁₃H₉NO₄
• 分子量: 243.219
• InChiKey: ZWQRSJSVYWEXHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4’-Nitrobiphenyl-3-carboxylic acid
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: 4’-Nitrobiphenyl-3-carboxylic acid
CAS number: 729-01-1

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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: C13H9NO4
Molecular weight: 243.2

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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-硝基联苯-3-羧酸 在 palladium on activated charcoal 正丁基锂 、 草酰氯 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 0.58h， 生成 4--3-<(triphenylmethyl)thio>propyl>amino>-3'-(tert-butoxycarbonyl)biphenyl
  参考文献：
  名称：

  设计和合成非肽Ras CAAX模拟物作为有效的法呢基转移酶抑制剂。

  摘要：

  ras癌基因产物Ras的半胱氨酸法呢基化对于其转化活性是必需的，并且被法呢基转移酶（FTase）催化。Ras羧基末端四肽CAAX（C是半胱氨酸，A是任何脂肪族氨基酸，X是蛋氨酸或丝氨酸）是FTase识别的最小序列。我们在这里报告Ras CAAX非肽模拟物的设计，合成和生物学特性，其中半胱氨酸通过还原的伪肽键与4-氨基-3'-羧基联苯相连。这些非肽模拟物是FTase的有效抑制剂（IC50 = 40 nM，是最有效的抑制剂），对FTase的选择性高于GGTase I（香叶基香叶基转移酶I）。它们不是法呢基化的底物，没有肽特征，也没有可水解键。结构活性研究揭示了芳基环上羧酸位置以及半胱氨酸酰胺键还原的重要性。在4-氨基-3'-羧基联苯的2-位取代可提高抑制能力，而羧酸的去除则会导致抑制活性降低10倍。

  DOI：

  10.1021/jm950414g
• 作为产物：
  描述：

  3-苯基苯甲酸 在 硝酸 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 4-硝基联苯-3-羧酸
  参考文献：
  名称：

  Derivatives of aminobenzoic and aminobiphenylcarboxylic acids useful as anti-cancer agents

  摘要：

  本发明提供具有以下结构的化合物： 其中n为0或1； R为—NH2或 其中R1和R2分别选自H、烷基、芳基烷基、杂环芳基、羧基、羧基烷基和氨基甲酰基的群组； Q为R3C(O)—或 其中R5选自H、烷基、芳基烷基、杂环芳基和氨基甲酰基烷基的群组，R3和R4选自H、烷基、烷氧基、芳基烷氧基、芳基烷基、杂环芳基和氨基甲酰基烷基的群组； 公式I化合物的Q—NH—(CH2)n—和—C(O)R取代基独立地相对于形成两个苯基之间的碳原子定位于邻位、间位或对位，但前提是这些取代基不会同时定位于邻位；以及 公式II化合物的Q—NH—(CH2)n和—C(O)R取代基相对于彼此定位于间位或对位； 或其生物可降解酯，或其药学上可接受的盐。这些化合物可用于治疗uPA或uPAR介导的疾病，例如肿瘤转移、肿瘤血管生成、再狭窄、慢性炎症或角膜血管生成。

  公开号：

  US06228985B1

文献信息

• Inhibitors of prenyl transferases
  申请人：Univeristy of Pittsburgh

  公开号：US05965539A1

  公开（公告）日：1999-10-12

  Compounds which inhibit prenyl transferases, particularly farnysyltransferase and geranylgeranyl transferase I, processes for preparing the compounds, pharmaceutical compositions containing the compounds, and methods of use.

  抑制戊二烯基转移酶，特别是戊二烯基转移酶和戊二烯基转移酶I的化合物，制备这些化合物的方法，含有这些化合物的药物组合物，以及使用方法。
• Inhibitors of protein isoprenyl transferases
  申请人：University of Pittsburgh

  公开号：US20020193596A1

  公开（公告）日：2002-12-19

  Compounds having the formula 1 or a pharmaceutically acceptable salt thereof wherein R 1 is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L 2 —, and (i) heterocyclic-L 2 —; R 2 is selected from (a) 2 (b) —C(O)NH—CH(R 14 )—C(O)OR 15 , (c) 3 (d) —C(O)NH—CH(R 14 )—C(O)NHSO 2 R 16 (e) —C(O)NH—CH(R 14 )-tetrazolyl, (f) —C(O)NH-heterocyclic, and (g) —C(O)NH—CH(R 14 )—C(O)NR 17 R 18 ; R 3 is heterocyclic, aryl, substituted or unsubstituted cycloalkyl; R 4 is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L 1 is absent or is selected from (a) —L 4 —N(R 5 )—L 5 —, (b) —L 4 —O—L 5 —, (c) —L 4 —S(O) n —L 5 — (d) —L 4 -L 6 —C(W)—N(R 5 )—L 5 —, (e) —L 4 -L 6 —S(O) m —N(R 5 )—L 5 —, (f) —L 4 —N(R 5 )—C(W)—L 7 -L 5 —, (g) —L 4 —N(R 5 )—S(O) p —L 7 —L 5 —, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, and (j) optionally substituted alkynylene are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.

  具有以下公式的化合物或其药学上可接受的盐，其中R1为(a)氢，(b)较低的烷基，(c)烯基，(d)烷氧基，(e)硫代烷氧基，(f)卤素，(g)卤代烷基，(h)芳基-L2—，以及(i)杂环-L2—；R2从(a)中选择，(b) -C(O)NH-CH(R14)-C(O)OR15，(c)中选择，(d) -C(O)NH-CH(R14)-C(O)NHSO2R16，(e) -C(O)NH-CH(R14)-四唑基，(f) -C(O)NH-杂环，以及(g) -C(O)NH-CH(R14)-C(O)NR17R18；R3为杂环，芳基，取代或未取代的环烷基；R4为氢，较低烷基，卤代烷基，卤素，芳基，芳基烷基，杂环基，或(杂环)烷基；L1为空缺或从(a) -L4-N(R5)-L5-，(b) -L4-O-L5-，(c) -L4-S(O)n-L5-，(d) -L4-L6-C(W)-N(R5)-L5-，(e) -L4-L6-S(O)m-N(R5)-L5-，(f) -L4-N(R5)-C(W)-L7-L5-，(g) -L4-N(R5)-S(O)p-L7-L5-，(h)可选择取代的烷基，(i)可选择取代的烯基，以及(j)可选择取代的炔基是蛋白异戊二烯转移酶的抑制剂。还公开了蛋白异戊二烯转移酶抑制组合物和抑制蛋白异戊二烯转移酶的方法。
• Discovery and development of novel salicylate synthase (MbtI) furanic inhibitors as antitubercular agents
  作者：Laurent R. Chiarelli、Matteo Mori、Daniela Barlocco、Giangiacomo Beretta、Arianna Gelain、Elena Pini、Marianna Porcino、Giorgia Mori、Giovanni Stelitano、Luca Costantino、Margherita Lapillo、Davide Bonanni、Giulio Poli、Tiziano Tuccinardi、Stefania Villa、Fiorella Meneghetti

  DOI：10.1016/j.ejmech.2018.06.033

  日期：2018.7

  evaluation of new furan derivatives targeting Mycobacterium tuberculosis salicylate synthase (MbtI). A receptor-based virtual screening procedure was applied to screen the Enamine database, identifying two compounds, I and III, endowed with a good enzyme inhibitory activity. Considering the most active compound I as starting point for the development of novel MbtI inhibitors, we obtained new derivatives

  我们报告针对结核分枝杆菌水杨酸合酶（MbtI）的新呋喃衍生物的虚拟筛选，合成和生物学评估。应用基于受体的虚拟筛选程序筛选Enamine数据库，鉴定出具有良好酶抑制活性的两种化合物I和III。考虑到最具活性的化合物I作为开发新型MbtI抑制剂的起点，我们获得了基于呋喃支架的新衍生物。在此类SAR中，化合物1a成为迄今为止报道的最有效的MbtI抑制剂（K i  = 5.3μM ）。此外，化合物1a表现出有希望的抗 分枝杆菌活性（MIC 99 = 156μM），这可能与分枝杆菌素的生物合成抑制有关。
• Biaryl derived amide modulators of vanilloid VR1 receptor
  申请人：Codd Ellen

  公开号：US20060223837A1

  公开（公告）日：2006-10-05

  The invention is directed to novel vanilloid receptor type 1 (VR1) ligands. More specifically, the invention relates to novel biaryl-derived amides that are potent antagonists or agonists of VR1. Pharmaceutical and veterinary compositions and methods of treating mild to severe pain and various diseases using compounds of the invention are also described.

  该发明涉及新型辣椒素受体类型1（VR1）配体。更具体地，该发明涉及新型联苯基衍生酰胺，这些酰胺是VR1的有效拮抗剂或激动剂。还描述了利用该发明化合物治疗轻度至严重疼痛和各种疾病的药物和兽医组合物以及治疗方法。
• The preparation and acetolysis of some [π-phenylchromium tricarbonyl]benzyl p-toluenesulfonates and their noncomplexed analogs. a search for σπ delocalization
  作者：Robert S. Bly、Kuen-Kwong Tse、Ruta K. Bly

  DOI：10.1016/s0022-328x(00)87984-x

  日期：1976.8

  The substituted benzyl tosylates p-phenyl, p-(π-phenylchromium tricarbonyl), p-(p′-nitrophenyl), m-phenyl, m-(π-phenylchromium tricarbonyl) and m-(p′-nitrophenyl) have been prepared and their solvolysis rates in buffered and/or unbuffered acetic acid determined. At 69.0°C their reactivities relative to benzyl tosylate (1.00) are: 10.8, 7.14, 0.742, 0.571, 0.134 and 0.173, respectively. Conjugative

  取代的苄基甲苯磺酸酯p -苯基，p - （π-phenylchromium三羰基），p - （p '硝基苯基），米-苯基，米- （π-phenylchromium三羰基）和米- （p '硝基苯基）已制备以及它们在缓冲和/或非缓冲乙酸中的溶剂分解速率。在69.0℃下，它们相对于甲苯磺酸苄酯（1.00）的反应性分别为：10.8、7.14、0.742、0.571、0.134和0.173。共轭的取代基参数是在69℃计算p硝基苯（σ米+ 0.221，σ p +0.060）和π-phenylchromium三羰基（σ米+ 0.262，σ p + （0.144）。α-（π-phenylchromium三羰基）来稳定电子中心的能力与α二茂铁和电子供给的机构相比讨论过。