3-氨基-5-溴-2-苯并呋喃羧酸乙酯 | 330555-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-氨基-5-溴-2-苯并呋喃羧酸乙酯
• 中文别名: 乙基3-氨基-5-溴-1-苯并呋喃-2-羧酸
• 英文名称: ethyl 3-amino-5-bromo-1-benzofuran-2-carboxylate
• 英文别名: ethyl 5-bromo-3-amino-2-benzofurancarboxylate
• CAS: 330555-71-0
• 化学式: C₁₁H₁₀BrNO₃
• mdl: MFCD00454292
• 分子量: 284.109
• InChiKey: NPRPLFNZHAIWEC-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157°
• 沸点：
  382.0±37.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932999099
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,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: Ethyl 3-amino-5-bromo-1-benzofuran-2-carboxylate
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: Ethyl 3-amino-5-bromo-1-benzofuran-2-carboxylate
CAS number: 330555-71-0

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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: C11H10BrNO3
Molecular weight: 284.1

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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, hydrogen bromide.

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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-氨基-5-溴-2-苯并呋喃羧酸乙酯 在 正丁基锂 、 偶氮二甲酸二异丙酯 、 ammonium acetate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 反应 11.0h， 生成 8-Bromo-4-[6-(methylamino)pyridin-3-yl]-1-[2-(oxolan-2-yl)ethyl]-[1]benzofuro[3,2-d]pyrimidin-2-one
  参考文献：
  名称：

  [EN] CONDENSED TRICLYCLIC COMPOUNDS AS INHIBITORS OF HIV REPLICATION
  [FR] COMPOSÉS TRICYCLIQUES CONDENSÉS EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIH

  摘要：

  公式（I）的化合物及其制药组合物：其中A1、A2和A3分别独立地选自N和CR3组成的群，其中R1是可选择地取代的杂环烷基或可选择地取代的-(C1-6)烷基-杂环烷基，R2是可选择地取代的芳基或可选择地取代的杂芳基，R4是可选择地取代的芳基、可选择地取代的杂环烷基或可选择地取代的杂芳基，用作HIV复制抑制剂。

  公开号：

  WO2013091096A1
• 作为产物：
  描述：

  5-溴-2-羟基苯甲腈 在 sodium hydride 、 potassium carbonate 作用下， 生成 3-氨基-5-溴-2-苯并呋喃羧酸乙酯
  参考文献：
  名称：

  具有半胱氨酰白三烯受体2拮抗活性的3-乙酰乙酰氨基苯并[b]呋喃衍生物的制备。

  摘要：

  通过3-氨基苯并[b]呋喃与5-甲基异恶唑-4-羧酸氯的酰化反应，然后对异恶唑环进行碱性裂解，制备了在3-位具有修饰的三烯系统的新型3-乙酰乙酰氨基苯并[b]呋喃衍生物。这些化合物中的几种显示出中等的半胱氨酰白三烯受体2拮抗活性。

  DOI：

  10.1039/b307468d

文献信息

• Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity
  作者：Kumiko Ando、Eriko Tsuji、Yuko Ando、Noriko Kuwata、Jun-ichi Kunitomo、Masayuki Yamashita、Shunsaku Ohta、Shigekatsu Kohno、Yoshitaka Ohishi

  DOI：10.1039/b312682j

  日期：——

  Novel 3-acetoacetylaminobenzo[b]furan derivatives having a modified triene system at the 3-position were synthesized starting with 3-aminobenzo[b]furans. The enol isomers, 3-[(3-hydroxybut-2-enonyl)amino]benzo[b]furans (), of the 3-acetoacetylaminobenzo[b]furans were obtained as stable isomers owing to formation of a hydrogen bonding between the enol hydroxyl group and the amidocarbonyl group. The

  从3-氨基苯并[b]呋喃开始，合成了在3-位具有修饰的三烯系统的新型3-乙酰乙酰氨基苯并[b]呋喃衍生物。由于3-烯丙基乙酰氨基苯并[b]呋喃之间形成氢键，因此作为稳定异构体获得了3-乙酰基乙酰氨基苯并[b]呋喃的烯醇异构体3-[（3-羟基丁-2-烯丙基）氨基]苯并[b]呋喃。羟基和酰胺羰基。通过C-3侧链的C-2取代基的平面性表明烯醇化合物中存在改性的共轭三烯系统。评估了半胱氨酸白三烯1和2受体对这些化合物的拮抗活性。2-（4-氰基苯甲酰基或乙氧基羰基）-3-[（2-氰基-3-羟基丁-2-烯丙基）氨基]苯并[b]呋喃（，）具有中等活性。
• INHIBITORS OF HIV REPLICATION
  申请人：STURINO Claudio

  公开号：US20100261714A1

  公开（公告）日：2010-10-14

  Compounds of formula (I): wherein R 1 , R 2 , A 1 , A 2 , A 3 , A 4 , X and Y are as defined herein, are useful as inhibitors of HIV replication.

  式(I)的化合物： 其中R1、R2、A1、A2、A3、A4、X和Y如本文所定义，可用作HIV复制抑制剂。
• Identification and Characterization of a Novel HIV-1 Nucleotide-Competing Reverse Transcriptase Inhibitor Series
  作者：D. Rajotte、S. Tremblay、A. Pelletier、P. Salois、L. Bourgon、R. Coulombe、S. Mason、L. Lamorte、C. F. Sturino、R. Bethell

  DOI：10.1128/aac.00113-13

  日期：2013.6

  Several groups have recently reported on the identification of nucleotide-competing reverse transcriptase inhibitors (NcRTIs), a new class of RT inhibitors. NcRTIs reversibly inhibit binding of the incoming nucleotide to the RT active site but do not act as chain terminators, unlike the nucleos(t)ide reverse transcriptase inhibitor (NRTI) class. We identified a novel benzo[4,5]furo[3,2, d ]pyrimidin-2-one NcRTI chemical series. Structure-activity relationship evaluation of this series with both RT and viral replication assays led to the identification of compound A, a new NcRTI. Compound A inhibited HIV-1 RT in a primer extension assay (50% inhibitory concentration, 2.6 nM) but had no measurable activity against human DNA polymerase γ at 10 μM. It potently inhibited HIV-1 replication in vitro (50% effective concentration, 1.5 nM). The antiviral potency of compound A was unaffected by the presence of nonnucleotide RT inhibitor (NNRTI) mutations tested (L100I, K103N/Y181C, V106A, or Y188L). Notably, viruses encoding K65R were hypersusceptible to inhibition by compound A. Compound A also retained full activity against viruses encoding M184V. In vitro selection for resistant virus to compound A led to the selection of a single substitution within RT: W153L. A recombinant virus encoding the RT W153L was highly resistant to compound A (fold change, 160). W153 is a highly conserved residue in HIV RT and has not been previously associated with drug resistance. In summary, a novel NcRTI series with optimized antiviral activity, minimal cross-resistance to existing RT inhibitor classes, and a distinct resistance profile has been discovered. These results further establish NcRTIs as an emerging class of antiretroviral agents.

  摘要 最近有几个研究小组报告了核苷酸竞争性逆转录酶抑制剂（NcRTIs）的鉴定结果，这是一类新的 RT 抑制剂。NcRTIs 可逆性地抑制输入核苷酸与 RT 活性位点的结合，但与核苷（t）ide 逆转录酶抑制剂（NRTI）类不同，不作为链终止剂。我们发现了一种新型苯并[4,5]呋喃并[3,2、 d 嘧啶-2-酮 NcRTI 化学系列。利用 RT 和病毒复制试验对该系列进行了结构-活性关系评估，最终确定了化合物 A，这是一种新型 NcRTI。化合物 A 在引物延伸试验中抑制 HIV-1 RT（50% 抑制浓度，2.6 nM），但在 10 μM 时对人类 DNA 聚合酶 γ 没有可测量的活性。它能有效抑制 HIV-1 体外 (50％ 有效浓度，1.5 nM）。化合物 A 的抗病毒效力不受测试的非核苷酸 RT 抑制剂（NNRTI）突变（L100I、K103N/Y181C、V106A 或 Y188L）的影响。值得注意的是，编码 K65R 的病毒对化合物 A 的抑制作用不敏感。 体外 体外筛选对化合物 A 产生抗性的病毒时，在 RT：W153L。编码 RT W153L 的重组病毒对化合物 A 具有很强的抗药性（折叠变化，160）。W153 是 HIV RT 中一个高度保守的残基，以前从未发现它与耐药性有关。总之，我们发现了一种新型 NcRTI 系列，它具有优化的抗病毒活性、对现有 RT 抑制剂类的交叉耐药性最小以及独特的耐药性特征。这些结果进一步确立了 NcRTIs 作为一类新兴抗逆转录病毒药物的地位。
• Nucleotide competing reverse transcriptase inhibitors: Discovery of a series of non-basic benzofurano[3,2-d]pyrimidin-2-one derived inhibitors
  作者：Clint A. James、Patrick DeRoy、Martin Duplessis、Paul J. Edwards、Teddy Halmos、Joannie Minville、Louis Morency、Sébastien Morin、Bruno Simoneau、Martin Tremblay、Richard Bethell、Michael Cordingley、Jianmin Duan、Louie Lamorte、Alex Pelletier、Daniel Rajotte、Patrick Salois、Sonia Tremblay、Claudio F. Sturino

  DOI：10.1016/j.bmcl.2013.02.021

  日期：2013.5

  A HTS screen led to the identification of a benzofurano[3,2-d]pyrimidin-2-one core structure which upon further optimization resulted in 1 as a potent HIV-1 nucleotide competing reverse transcriptase inhibitor (NcRTI). Investigation of the SAR at N-1 allowed significant improvements in potency and when combined with the incorporation of heterocycles at C-8 resulted in potent analogues not requiring a basic amine to achieve antiviral activity. Additional modifications at N-1 resulted in 33 which demonstrated excellent antiviral potency and improved physicochemical properties. (C) 2013 Published by Elsevier Ltd.
• Basawaraj, Raja; Chavan, Varsha; Patil, Ashok, Indian Journal of Heterocyclic Chemistry, 2010, vol. 20, # 2, p. 129 - 132
  作者：Basawaraj, Raja、Chavan, Varsha、Patil, Ashok、Upendra、Gandhi, Narasimha、Noola, Shivanand、Vijaykumar、Naubade, Kashinath

  DOI：——

  日期：——