8H-茚并[1,2-d]噻唑-2-胺 | 85787-95-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 8H-茚并[1,2-d]噻唑-2-胺
• 英文名称: 8H-indeno[1,2-d]thiazol-2-amine
• 英文别名: 8H-indeno[1,2-d][1,3]thiazol-2-amine；4H-indeno[1,2-d][1,3]thiazol-2-amine
• CAS: 85787-95-7
• 化学式: C₁₀H₈N₂S
• mdl: MFCD08689683
• 分子量: 188.253
• InChiKey: XXHWFLFMSNXBLK-UHFFFAOYSA-N

物化性质

• 熔点：
  268-270
• 沸点：
  399.6±11.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 8H-Indeno[1,2-d][1,3]thiazol-2-amine
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 8H-Indeno[1,2-d][1,3]thiazol-2-amine
CAS number: 85787-95-7

---

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.
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: C10H8N2S
Molecular weight: 188.2

---

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, sulfur 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：

  8H-茚并[1,2-d]噻唑-2-胺 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以85%的产率得到(3aR,4S,7R,7aS)-2-(8H-indeno[1,2-d]thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
  参考文献：
  名称：

  新型 2-(4-(Aryl)thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione 衍生物的合成及碳酸酐酶抑制

  摘要：

  碳酸酐酶 (CA, EC 4.2.1.1) 是金属酶家族的成员。它催化二氧化碳 (CO2) 和水快速转化为碳酸氢盐 (HCO3-) 和质子 (H+)，并且在生化和生理过程中也起着重要作用。在这项研究中，一些新的 2-(4-(芳基)噻唑-2-基)-3a,4,7,7a-四氢-1H-4,7-methanoisoindole-1,3(2H)-dione 衍生物合成并评估了它们对人 CA 同工酶 I 和 II（hCA I 和 hCA II）的抑制特性。新分子 8a-i 的结构通过 IR、1H NMR、13C NMR 和元素分析得到证实。这些化合物在低纳摩尔范围内表现出优异的抑制作用，对 hCA I 的 Ki 值在 27.07-37.80 nM 的范围内，对 hCA II 的 Ki 值在 11.80-25.81 nM 的范围内。

  DOI：

  10.1002/ardp.201600092
• 作为产物：
  描述：

  8H-indeno[1,2-d]thiazol-2-ylamine hydroiodid 在 水 作用下， 以 sodium hydroxide 为溶剂， 反应 1.0h， 以to provide 5.30 g of 8H-Indeno[1,2-d]thiazol-2-ylamine 1b的产率得到8H-茚并[1,2-d]噻唑-2-胺
  参考文献：
  名称：

  Substituted N-acyl-2-aminothiazoles

  摘要：

  提供了公式或其药学上可接受的盐的化合物，可用于治疗糖尿病、糖尿病视网膜病变、哮喘和腹泻。

  公开号：

  US07407977B2

文献信息

• Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)
  作者：Chunhua Ma、Yuqi Miao、Minghao Zhao、Ping Wu、Jianglu Zhou、Zhi Li、Xilei Xie、Wei Zhang

  DOI：10.1016/j.tet.2018.05.021

  日期：2018.7

  An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to

  据报道，通过DBH介导的苯乙烯和硫脲的氧化环化合成2-氨基噻唑的有效方法。使用DBH作为溴源和氧化剂，通过两步一锅法成功地将各种烯烃成功转化为相应的2-氨基噻唑，产率为10-81％。该方法可以容易地以克为单位进行，并且成功地用于以苯乙烯为起始原料的抗炎药fanetizole的合成。
• Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions
  作者：Honnappa Nagarajaiah、Abhaya Kumar Mishra、Jarugu Narasimha Moorthy

  DOI：10.1039/c6ob00351f

  日期：——

  ball-milling conditions – were set up for a sequential base-mediated condensation reaction with thiourea/thiosemicarbazides, o-phenylenediamine and salicylaldehyde to afford 2-aminothiazoles, 2-hydrazinylthiazoles, quinoxalines and benzoylbenzofurans, respectively, in respectable yields. The viability of one-pot sequential acid- and base-mediated reactions in the solid state under ball-milling conditions

  α氯酮-通过用三氯异氰尿酸（TCCA）在存在酮的原子经济氯化得到的p被设置为与硫脲/氨基硫脲，顺序碱介导的缩合反应- -tsa球磨条件下ö -苯二胺和水杨醛分别以可观的收率得到2-氨基噻唑，2-肼基噻唑，喹喔啉和苯甲酰基苯并呋喃。因此证明了在球磨条件下一锅顺序酸和碱介导的固态反应的可行性。
• Synthesis and antibacterial screening of novel 2-(4-(aryl) thiazol-2-yl)-3a,4,7,7a-tetrahydro-1<i>H</i>-4,7-ethanoisoindole-1,3(2<i>H</i>)-dione derivatives
  作者：Oguz Özbek、Necibe Canan Usta、Meliha Burcu Gürdere、Osman Nuri Aslan、Yakup Budak、Mustafa Ceylan

  DOI：10.1080/10426507.2017.1354209

  日期：2017.10.3

  GRAPHICAL ABSTRACT ABSTRACT A series of novel 2-(4-(aryl)thiazol-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3(2H)-dione derivatives were synthesized and evaluated for their antimicrobial activity. The structures of the synthesized derivatives (9a-j) were confirmed by means of IR, 1H-NMR, 13C-NMR and elemental analyses. All the compounds 9a-j showed activity against all microorganisms. Compounds

  图形摘要 摘要 一系列新型 2-(4-(芳基)噻唑-2-基)-3a,4,7,7a-四氢-1H-4,7-ethanoisoindole-1,3(2H)-dione 衍生物是合成并评估其抗菌活性。合成衍生物(9a-j)的结构通过IR、1H-NMR、13C-NMR和元素分析证实。所有化合物9a-j均显示出针对所有微生物的活性。化合物 9a、9c-d 和 9j 对测试的化脓性链球菌表现出有效的抗菌活性。化合物 9c 对产气荚膜梭菌显示出比标准品更高的活性。9a-e、9j 和 9i 对 A. tumefacen 具有良好的活性。
• New Positive Ca²⁺-Activated K⁺ Channel Gating Modulators with Selectivity for K_Ca3.1
  作者：Nichole Coleman、Brandon M. Brown、Aida Oliván-Viguera、Vikrant Singh、Marilyn M. Olmstead、Marta Sofia Valero、Ralf Köhler、Heike Wulff

  DOI：10.1124/mol.114.093286

  日期：2014.9

  Small-conductance (KCa2) and intermediate-conductance (KCa3.1) calcium-activated K+ channels are voltage-independent and share a common calcium/calmodulin-mediated gating mechanism. Existing positive gating modulators like EBIO, NS309, or SKA-31 activate both KCa2 and KCa3.1 channels with similar potency or, as in the case of CyPPA and NS13001, selectively activate KCa2.2 and KCa2.3 channels. We performed a structure-activity relationship (SAR) study with the aim of optimizing the benzothiazole pharmacophore of SKA-31 toward KCa3.1 selectivity. We identified SKA-111 (5-methylnaphtho[1,2- d ]thiazol-2-amine), which displays 123-fold selectivity for KCa3.1 (EC50 111 ± 27 nM) over KCa2.3 (EC50 13.7 ± 6.9 μ M), and SKA-121 (5-methylnaphtho[2,1- d ]oxazol-2-amine), which displays 41-fold selectivity for KCa3.1 (EC50 109 nM ± 14 nM) over KCa2.3 (EC50 4.4 ± 1.6 μ M). Both compounds are 200- to 400-fold selective over representative KV (KV1.3, KV2.1, KV3.1, and KV11.1), NaV (NaV1.2, NaV1.4, NaV1.5, and NaV1.7), as well as CaV1.2 channels. SKA-121 is a typical positive-gating modulator and shifts the calcium-concentration response curve of KCa3.1 to the left. In blood pressure telemetry experiments, SKA-121 (100 mg/kg i.p.) significantly lowered mean arterial blood pressure in normotensive and hypertensive wild-type but not in KCa3.1−/− mice. SKA-111, which was found in pharmacokinetic experiments to have a much longer half-life and to be much more brain penetrant than SKA-121, not only lowered blood pressure but also drastically reduced heart rate, presumably through cardiac and neuronal KCa2 activation when dosed at 100 mg/kg. In conclusion, with SKA-121, we generated a KCa3.1-specific positive gating modulator suitable for further exploring the therapeutical potential of KCa3.1 activation.

  小电导（KCa2）和中电导（KCa3.1）钙激活 K+ 通道与电压无关，具有共同的钙/钙调素介导的门控机制。现有的正门控调节剂（如 EBIO、NS309 或 SKA-31）能以类似的效力激活 KCa2 和 KCa3.1 通道，或者像 CyPPA 和 NS13001 那样选择性地激活 KCa2.2 和 KCa2.3 通道。我们进行了一项结构-活性关系 (SAR) 研究，目的是优化 SKA-31 的苯并噻唑药理结构，使其具有 KCa3.1 选择性。我们确定了 SKA-111（5-甲基萘并[1,2-d]噻唑-2-胺），它对 KCa3.1 的选择性（EC50 111 ± 27 nM）是 KCa2.3 的 123 倍（EC50 13.7 ± 6.9 μ M）和 SKA-121 （5-甲基萘并[2,1-d]恶唑-2-胺），后者对 KCa3.1 的选择性（EC50 109 nM ± 14 nM）是 KCa2.3 的选择性（EC50 4.4 ± 1.6 μ M）的 41 倍。这两种化合物对代表性 KV（KV1.3、KV2.1、KV3.1 和 KV11.1）、NaV（NaV1.2、NaV1.4、NaV1.5 和 NaV1.7）以及 CaV1.2 通道的选择性均为 200 到 400 倍。SKA-121 是一种典型的正通路调节剂，能使 KCa3.1 的钙离子浓度反应曲线向左移动。在血压遥测实验中，SKA-121（100 mg/kg i.p.）能显著降低血压正常和高血压野生型小鼠的平均动脉血压，但不能降低 KCa3.1-/- 小鼠的平均动脉血压。在药代动力学实验中发现，SKA-111 的半衰期比 SKA-121 长得多，对大脑的渗透性也更强，当剂量为 100 毫克/公斤时，SKA-121 不仅能降低血压，还能大幅降低心率，这可能是通过激活心脏和神经元 KCa2 实现的。总之，我们利用 SKA-121 生成了一种 KCa3.1 特异性正向门控调节剂，适合进一步探索 KCa3.1 激活的治疗潜力。
• Structure-based virtual screening discovers potent and selective adenosine A1 receptor antagonists
  作者：Pierre Matricon、Anh TN. Nguyen、Duc Duy Vo、Jo-Anne Baltos、Mariama Jaiteh、Andreas Luttens、Stefanie Kampen、Arthur Christopoulos、Jan Kihlberg、Lauren Therese May、Jens Carlsson

  DOI：10.1016/j.ejmech.2023.115419

  日期：2023.9

  could be exploited to identify AR selective ligands. A library of 4.6 million compounds was screened computationally against both receptors using molecular docking and 20 AR selective ligands were predicted. Of these, seven antagonized the AR with micromolar activities and several compounds displayed slight selectivity for this subtype. Twenty-seven analogs of two discovered scaffolds were designed, resulting

  开发亚型选择性先导化合物对于针对 G 蛋白偶联受体 (GPCR) 的药物发现活动至关重要。在此，将基于结构的虚拟筛选方法合理设计亚型选择性配体，应用于 A 和 A 腺苷受体（AR 和 AR）。这些密切相关的亚型的晶体结构揭示了结合位点中的非保守亚袋，可用于识别 AR 选择性配体。使用分子对接针对两种受体对包含 460 万种化合物的库进行了计算筛选，并预测了 20 个 AR 选择性配体。其中，七种化合物具有微摩尔活性拮抗 AR，并且几种化合物对该亚型表现出轻微的选择性。设计了两种已发现支架的 27 种类似物，产生了具有纳摩尔效力和高达 76 倍 AR 选择性的拮抗剂。我们的结果显示了基于结构的虚拟筛选在指导亚型选择性配体的发现和优化方面的潜力，这可以促进更安全药物的开发。