[1-(苯磺酰基)-1H-碘-3-基]甲醇 | 89241-33-8

• 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: [1-(苯磺酰基)-1H-碘-3-基]甲醇
• 英文名称: (1-(phenylsulfonyl)-1H-indol-3-yl)methanol
• 英文别名: 1-(phenylsulfonyl)-3-(hydroxymethyl)indole；(1-benzenesulfonyl-1H-indol-3-yl)-methanol；[1-(Phenylsulfonyl)-1H-Indol-3-Yl]Methanol；[1-(benzenesulfonyl)indol-3-yl]methanol
• CAS: 89241-33-8
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: ZMLXSFMIPYDHIN-UHFFFAOYSA-N

物化性质

• 熔点：
  90 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 安全说明：
  S24/25

SDS

Name:	[1-(Phenylsulfonyl)-1H-indol-3-yl]methanol 97% Material Safety Data Sheet
Synonym:
CAS:	89241-33-8

Section 1 - Chemical Product MSDS Name:[1-(Phenylsulfonyl)-1H-indol-3-yl]methanol 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
89241-33-8	[1-(Phenylsulfonyl)-1H-indol-3-yl]meth	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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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:
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# 89241-33-8: Personal Protective Equipment Eyes: Not available.
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: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 86 - 90 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: C15H13NO3S
Molecular Weight: 287.34

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 89241-33-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
[1-(Phenylsulfonyl)-1H-indol-3-yl]methanol - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 89241-33-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 89241-33-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 89241-33-8 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：

  [1-(苯磺酰基)-1H-碘-3-基]甲醇 在 咪唑 、 N-氯代丁二酰亚胺 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 N-(biphenyl-4-ylmethyl)-3-(hydroxymethyl)-1-(phenylsulfonyl)-1H-indole-2-sulfonamide
  参考文献：
  名称：

  吲哚磺酰胺作为大麻素受体阴性变构调节剂的开发。

  摘要：

  现有的CB1阴性变构调节剂（NAM）属于结构类别的有限范围。尽管具有CB1 NAM的理论潜力，但已发表的体内研究通常不能证明预期的与治疗相关的CB1介导的作用。因此，需要更大范围的分子工具才能明确阐明CB1变构调节作用。在这项研究中，我们显示了一系列新颖的吲哚磺酰胺。化合物5e和6c（ABD1075）的效力分别为4和3nM，并显示出良好的口服暴露和CNS渗透性，使其成为研究大麻素系统的变构调节作用的潜在治疗工具。

  DOI：

  10.1016/j.bmcl.2016.08.018
• 作为产物：
  描述：

  N-苯磺酰基-3-(溴甲基)吲哚 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 [1-(苯磺酰基)-1H-碘-3-基]甲醇
  参考文献：
  名称：

  Babu, Suresh D.; Hrytsak, Michael D.; Durst, Tony, Canadian Journal of Chemistry, 1989, vol. 67, p. 1071 - 1076

  摘要：

  DOI：

文献信息

• [EN] N-ARYLSULFONYL-3-SUBSTITUTED INDOLES HAVING SEROTONIN RECEPTOR AFFINITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM<br/>[FR] INDOLES N-ARYLSULFONYL-3-SUBSTITUES PRESENTANT UNE AFFINITE POUR LE RECEPTEUR DE LA SEROTONINE, METHODE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE CONTENANT CES INDOLES
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2004048330A1

  公开（公告）日：2004-06-10

  The present invention relates to novel N-arylsulfonyl-3-substituted indole compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their geometric forms, their N-oxides, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel N-arylsulfonyl-3-substituted indoles of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, and pharmaceutically acceptable compositions containing them. This invention also relates to the process for preparing compounds of the general formula (I), pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine. This invention also relates to the novel intermediates involved therein and process of their preparation.

  本发明涉及新型的N-芳基亚磺酰基-3-取代吲哚化合物、其衍生物、类似物、互变异构体、立体异构体、几何异构体、N-氧化物、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明特别涉及具有通用公式(I)的新型N-芳基亚磺酰基-3-取代吲哚、其衍生物、类似物、互变异构体、立体异构体、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明还涉及制备通用公式(I)化合物的过程、含有此类化合物的药物组合物以及此类化合物和组合物在医学中的用途。本发明还涉及其中涉及的新中间体及其制备过程。
• Discovery and Development of 1-[(2-Bromophenyl)sulfonyl]-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]-1<i>H</i>-indole Dimesylate Monohydrate (SUVN-502): A Novel, Potent, Selective and Orally Active Serotonin 6 (5-HT₆) Receptor Antagonist for Potential Treatment of Alzheimer’s Disease
  作者：Ramakrishna Nirogi、Anil Shinde、Rama Sastry Kambhampati、Abdul Rasheed Mohammed、Sangram Keshari Saraf、Rajesh kumar Badange、Thrinath Reddy Bandyala、Venugopalarao Bhatta、Kumar Bojja、Veena Reballi、Ramkumar Subramanian、Vijay Benade、Raghava Choudary Palacharla、Gopinadh Bhyrapuneni、Pradeep Jayarajan、Vinod Goyal、Venkat Jasti

  DOI：10.1021/acs.jmedchem.6b01662

  日期：2017.3.9

  04 nM) and selectivity over 100 target sites which include receptors, enzymes, peptides, growth factors, ion channels, steroids, immunological factors, second messengers, and prostaglandins. It has high selectivity over 5-HT2A receptor. It is orally bioavailable and brain penetrant with robust preclinical efficacy. The combination of 5al, donepezil, and memantine (triple combination) produces synergistic

  优化一系列新型的3-（哌嗪基甲基）吲哚衍生物作为5-羟基色胺-6受体（5-HT 6 R）拮抗剂可导致鉴定出1-[（（2-溴苯基）磺酰基] -5-甲氧基-3- [ （4-甲基-1-哌嗪基）甲基] -1 H-吲哚二甲酸酯一水合物（5al，SUVN-502）作为潜在治疗认知障碍的临床候选药物。它对人5-HT 6 R具有高亲和力（K i = 2.04 nM），对100个靶位具有选择性，这些靶位包括受体，酶，肽，生长因子，离子通道，类固醇，免疫学因子，第二信使和前列腺素。它具有超过5-HT 2A的高选择性受体。它具有口服生物利用度和脑渗透性，并具有强大的临床前功效。的组合5AL，多奈哌齐，美金刚和（三联组合）产生在腹侧海马乙酰胆碱的细胞外水平的协同效应。三联组合的临床前功效和对5-HT 2A受体的高选择性是区别特征，最终决定了5al的进一步开发。安全性和药代动力学的第一阶段评估已经完成，从而可以启动第二阶段概念验证研究。
• Intramolecular Diels-Alder Reactions of 4H-Furo[3,4-b]indoles. New Syntheses of Benzo[a]carbazoles and Benzo[c]carbazoles
  作者：Gordon W. Gribble、Richard A. Silva、Mark G. Saulnier

  DOI：10.1080/00397919908085823

  日期：1999.2

  Abstract Furoindoles 7 and 16 undergo smooth intramolecular Diels-Alder reactions to afford, after dehydration, hydrolysis, and oxidation, benzocarbazoles 11 and 21, respectively.

  摘要 呋喃吲哚 7 和 16 经历平滑的分子内 Diels-Alder 反应，在脱水、水解和氧化后分别得到苯并咔唑 11 和 21。
• Iron(II)-Catalyzed Asymmetric Intramolecular Aminohydroxylation of Indoles
  作者：Yong-Qiang Zhang、Yong-An Yuan、Guan-Sai Liu、Hao Xu

  DOI：10.1021/ol401666e

  日期：2013.8.2

  An enantioselective intramolecular indole aminohydroxylation reaction is catalyzed by iron(II)–chiral bisoxazoline (BOX) complexes (ee up to 99%, dr > 20:1). This discovery enables expedient asymmetric synthesis of a series of biologically active 3-amino oxindoles and 3-amino indolanes.

  铁（II）-手性双恶唑啉（BOX）配合物（ee高达99％，dr> 20：1）催化对映选择性分子内吲哚氨基羟化反应。这一发现使得一系列生物活性的3-氨基羟吲哚和3-氨基吲哚类化合物的非对称合成成为可能。
• Stereochemical Aspects of the Iodine(III)-Mediated Aziridination Reaction of Some Cyclic Allylic Carbamates
  作者：Albert Padwa、Thomas Stengel

  DOI：10.1021/ol0259490

  日期：2002.6.1

  [reaction: see text] The iodine(III)-mediated aziridination reaction of an indolyl-substituted carbamate requires a Rh(II) catalyst and proceeds by a metallonitrene intermediate. Stepwise addition across the indole pi-bond followed by Rh(II) detachment generates a metal-free zwitterion, which ultimately leads to the observed products. In contrast, intramolecular aziridination of several cycloalkenyl

  [反应：参见正文]吲哚基取代的氨基甲酸酯的碘（III）介导的叠氮化反应需要Rh（II）催化剂，并通过金属茂中间体进行。逐步添加到吲哚pi键上，然后进行Rh（II）分离，生成无金属的两性离子，最终生成了观察到的产物。相反，几种环烯基氨基甲酸酯的分子内叠氮化不需要Rh（II）催化剂，而是通过亚氨基碘烷中间体发生的。