四氢-6,7-异喹啉二醇 | 52768-23-7

• 物质功能分类: 医药中间体 - 异喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 四氢-6,7-异喹啉二醇
• 中文别名: 1,2,3,4-四氢-6,7-异喹啉二醇氢溴酸盐
• 英文名称: 1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide
• 英文别名: 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide；1,2,3,4-tetrahydroisoquinolin-2-ium-6,7-diol;bromide
• CAS: 52768-23-7
• 化学式: BrH*C₉H₁₁NO₂
• 分子量: 246.104
• InChiKey: LBDAQUYUIYKBKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.5
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933499090

SDS

Name:	1 2 3 4-Tetrahydro-6 7-isoquinolinediol hy drobromide 98% Material Safety Data Sheet
Synonym:
CAS:	52768-23-7

Section 1 - Chemical Product MSDS Name:1 2 3 4-Tetrahydro-6 7-isoquinolinediol hy drobromide 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
52768-23-7	1,2,3,4-Tetrahydro-6,7-isoquinolinedio		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 52768-23-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 210 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H11NO2.HBr
Molecular Weight: 246.10

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing materials.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 52768-23-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2,3,4-Tetrahydro-6,7-isoquinolinediol hydrobromide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 52768-23-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 52768-23-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 52768-23-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  四氢-6,7-异喹啉二醇 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0~70.0 ℃ 、275.79 kPa 条件下， 反应 23.0h， 生成 2-(3-hydroxy-3-phenylpropyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diyl diacetate
  参考文献：
  名称：

  新的[（芳基）（芳氧基）甲基]哌啶衍生物及相关化合物的合成和结合研究，它们对5-羟色胺（5-HT）和去甲肾上腺素（NE）转运蛋白具有高亲和力。

  摘要：

  在针对新型，高效，速效抗抑郁药的广泛搜索计划中，我们制备了一系列具有（芳基）（芳氧基）甲基部分的新化合物，这些化合物直接或通过亚甲基链连接至不同的取代和未取代环（异喹啉，哌嗪，哌啶，四氢吡喃或环戊烷）。已评估这些化合物对血清素（5-HT）转运蛋白（SERT）和5-HT（1A）和5-HT（2A）受体的亲和力。4-[（（芳基）（芳氧基）甲基]哌啶衍生物的外消旋混合物对SERT的亲和力值比氟西汀高得多，并导致对5-HT（1A）和5-HT（2A）受体的亲和力不足。这些外消旋混合物中的一些被拆分为其对映异构体，并测试与去甲肾上腺素（NE）转运蛋白（NET），多巴胺（DA）转运蛋白（DAT）和alpha（2）受体的结合。这些对映异构体中的几种[（-）-15b，（-）-15j，（-）-15t，（+）-15u]表现出对SERT和NET具有亲和力的K（i）<25 nM和a NET / SERT比率<10。化

  DOI：

  10.1021/jm0309349
• 作为产物：
  描述：

  6,7-二甲氧基-1,2,3,4-四氢异喹啉 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 四氢-6,7-异喹啉二醇
  参考文献：
  名称：

  儿茶酚反应性：6 位取代的多巴胺衍生物的合成

  摘要：

  摘要 多巴胺是一种普遍存在的神经递质，对人体的正常运作至关重要。除了这一关键作用之外，儿茶酚胺核心还显示出可用作多种药物和其他应用（如金属检测和粘合材料）的支架。多巴胺儿茶酚核心 6 位的取代基可以调节其立体电子特性、酚羟基的酸度和分子的整体疏水性。在此，我们报告了在儿茶酚核心的 6 位取代的一系列四种新型多巴胺类似物的合成。芳族质子间位到取代基的 1H NMR 化学位移与哈米特 σm 常数密切相关，证实了取代基的电子特性。图形概要

  DOI：

  10.1080/00397911.2016.1269350

文献信息

• 一种治疗糖尿病的化合物
  申请人：四川好医生药业集团有限公司

  公开号：CN103435612B

  公开（公告）日：2016-03-09

  本发明提供了式I所示的化合物或其药学上可接受的盐、水合物或溶剂合物。本发明还提供了上述化合物或其药学上可接受的盐、水合物或溶剂合物的新用途。本发明制备的氘代化合物，可以明显改善肥胖患者体重、空腹血糖、转氨酶和空腹血清胰岛素，提高胰岛素敏感性，改善血脂指标和口服葡萄糖耐量；该类化合物体内吸收良好，生物利用度高，有利于药效的发挥，且半衰期延长，可以减少给药次数，降低毒副作用，为临床用药提供了安全可靠的新选择。式I。
• 氮杂吲哚类化合物及其应用
  申请人：广州医科大学

  公开号：CN111606904B

  公开（公告）日：2021-10-15

  本发明提供了具有式(Ⅰ)所示结构的氮杂吲哚类化合物及其应用。该氮杂吲哚类化合物可以有效抑制SMAD3‑磷酸化，并且在大鼠LCC诱导的肿瘤模型中具有良好的抗肿瘤活性，并且，与化合物SIS3相比，部分本发明的氮杂吲哚类化合物显着改善了水溶性。本发明的氮杂吲哚类化合物有希望成为防治肿瘤的有效药物。
• Cephem Compounds with Latent Reactive Groups
  申请人：Gladius Pharmaceuticals, Inc.

  公开号：US20190100534A1

  公开（公告）日：2019-04-04

  Cephem and penem compounds having a styrylmethylene moiety at the 3-position in the cephem or penem ring to which a positively charged leaving group is bonded and wherein the leaving group contains a vicinal diol or is bonded to a unsubstituted or substituted catechol. The leaving group can be a positively charge nitrogen leaving group. Cephems include cephalosporins, cephamycins, carbacephems, and oxacephems. Penems include penems, carbapenems and oxapenems. Preferred cephems are cephalosporins. Preferred penems are carbapenems. Compounds exhibit antibiotic activity against Gram-negative bacteria and/or Gram-positive bacteria. Compounds exhibit antibiotic activity against bacteria which exhibit multi-drug resistance. Compounds of the invention exhibit antibiotic activity against bacterial strains which produce extended spectrum beta-lactamases (ESBL), which produce AmpC beta-lactamases or which produce a carbapenemase. Pharmaceutical compositions comprising one or more cephems or penems or methods of treatment of bacterial infections with such compounds and compositions.

  具有在头孢菌素或青霉烷素环中3位处具有苯乙烯亚甲基基团的头孢菌素和青霉烷素化合物，其中正电离子离去基团与离去基团中含有邻二醇或连接到未取代或取代过的邻苯二酚。离去基团可以是正电离子离去基团。头孢菌素包括头孢菌素、头孢菌烷、卡巴头孢菌素和氧头孢菌素。青霉烷素包括青霉烷素、碳青霉烷素和氧青霉烷素。首选头孢菌素是头孢菌素。首选青霉烷素是碳青霉烷素。化合物对革兰氏阴性细菌和/或革兰氏阳性细菌表现出抗生素活性。化合物对表现出多重耐药性的细菌表现出抗生素活性。本发明的化合物表现出抗生素活性，对产生扩展谱β-内酰胺酶（ESBL）、产生AmpCβ-内酰胺酶或产生碳青霉烷酶的细菌菌株表现出抗生素活性。包括一种或多种头孢菌素或青霉烷素的制药组合物或使用这些化合物和组合物治疗细菌感染的方法。
• MDR reversal agents
  申请人：——

  公开号：US05387685A1

  公开（公告）日：1995-02-07

  Compounds of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are herein described, A is a straight or branched (C.sub.2 -C.sub.12)alkyl or a phenyl moiety and B is a moiety of the formula: ##STR2## The compounds are effective in potentiating the activity of chemotherapeutic anti-cancer agents by increasing the sensitivity of multi-drug resistant cells to such chemotherapeutic agents.

  通式为：##STR1## 其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5如本文所述，A是直链或支链(C.sub.2 -C.sub.12)烷基或苯基基团，B是式的基团：##STR2## 这些化合物能够通过增加多药耐药细胞对化疗药物的敏感性，增强化疗抗癌药物的活性。
• Novel Benzo[<i>a</i>]quinolizidine Analogs Induce Cancer Cell Death through Paraptosis and Apoptosis
  作者：Hongbo Zheng、Yiwen Dong、Lin Li、Bin Sun、Lei Liu、Huiqing Yuan、Hongxiang Lou

  DOI：10.1021/acs.jmedchem.6b00484

  日期：2016.5.26

  massive endoplasmic reticulum (ER)- or mitochondria-derived vacuoles. Induction of paraptosis offers significant advantages for the treatment of chemotherapy-resistant tumors compared with anticancer drugs that rely on apoptosis. Because some natural alkaloids induce paraptotic cell death, a novel series of benzo[a]quinolizidine derivatives were synthesized, and their antiproliferative activity and ability

  截瘫是非凋亡性细胞死亡，其特征在于大量内质网（ER）或线粒体来源的液泡。与依赖凋亡的抗癌药物相比，诱发上pt裂可为化疗耐药性肿瘤的治疗提供显着优势。由于某些天然生物碱可诱导麻痹性细胞死亡，因此合成了一系列新的苯并[ a ]喹诺唑烷衍生物，并对其抗增殖活性和诱导细胞质空泡的能力进行了分析。结构优化导致了强效化合物22b的鉴定，该化合物在体内外抑制癌细胞的增殖，并极大地促进了类麻痹样细胞的死亡并诱导了caspase依赖性细胞凋亡。进一步调查发现22b介导的空泡作用源自持续的内质网应激和LC3B的上调。因此，由苯并[ a ]喹啉嗪衍生物诱导的截瘫代表了癌症化学疗法的另一种策略。