1-[2-氯-6-[[(3-碘苯基)甲基]氨基]-9h-嘌呤-9-基]-1-脱氧-N-甲基-beta-d-呋喃核糖酰胺 | 163042-96-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 1-[2-氯-6-[[(3-碘苯基)甲基]氨基]-9h-嘌呤-9-基]-1-脱氧-N-甲基-beta-d-呋喃核糖酰胺
• 英文名称: 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide
• 英文别名: Cl-IB-MECA；2-chloro-N⁶-(3-iodobenzyl)adenosine-5'-N-methyluronamide；2-Cl-IB-MECA；2-chloro-N⁶-(3-iodobenzyl)-5′-N-methylcarboxamidoadenosine；2-chloro-N⁶-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine；2-chloro-N⁶-(3-iodobenzyl)-adenosine-5′-N-methyluronamide；2-chloro-N⁶-(3-iodobenzyl)adenosine-5’-N-methyluronamide；2-chloro-N⁶-(3-iodobenzyl)adenosine-5'-N-methylcarboxamide；CF-102；Chloro-IB-MECA；(2S,3S,4R,5R)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• CAS: 163042-96-4
• 化学式: C₁₈H₁₈ClIN₆O₄
• 分子量: 544.736
• InChiKey: IPSYPUKKXMNCNQ-PFHKOEEOSA-N

物化性质

• 熔点：
  209 °C
• 密度：
  2.04±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  二甲基亚砜：>20mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2934999090
• 安全说明：
  S26
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  存储温度建议在0-10°C之间，并且要避免加热。

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Chloro-IB-MECA
CAS-No. : 163042-96-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Safety data sheet available on request.
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Cl-IB-MECA
2-Chloro-N6-(3-iodobenzyl)-adenosine-5′-N-methyluronamide
Formula : C18H18ClIN6O4
Molecular Weight : 544,73 g/mol
Component Concentration
Chloro-IB-MECA
CAS-No. 163042-96-4 -

---

Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

---

Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Hydrogen chloride gas, Hydrogen iodide
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

---

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 207 - 208 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

---

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

---

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

---

Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

---

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

---

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

---

Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

用途

2-Cl-IB-MECA用作A3腺苷受体选择性核苷。

生物活性

Namodenoson（CF-102，2-Cl-IB-MECA）是一种口服生物利用的A3腺苷受体(A3AR)的选择性激动剂，其Ki值为0.33 nM。Namodenoson通过失调PI3K/NF-κB/Wnt/β-catenin信号通路来发挥抗非酒精性脂肪肝病（NASH）的作用。

靶点

Target	Value
A3AR (细胞外实验)	0.33 nM(Ki)

反应信息

• 作为反应物：
  描述：

  1-[2-氯-6-[[(3-碘苯基)甲基]氨基]-9h-嘌呤-9-基]-1-脱氧-N-甲基-beta-d-呋喃核糖酰胺 在 sodium periodate 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以79%的产率得到(S)-2-((1R)-1-(2-chloro-6-(3-iodobenzylamino)-9H-purin-9-yl)-2-hydroxyethoxy)-3-hydroxy-N-methylpropanamide
  参考文献：
  名称：

  신규한 아데닌 유도체 및 그 용도

  摘要：

  本发明涉及新的腺嘌呤衍生物及其药理用途，更详细地说，涉及具有化学式1结构式的新的腺嘌呤衍生物或其药学上可接受的盐，以及用于预防或治疗退行性脑疾病的组合物。根据本发明的新腺嘌呤衍生物及其药学上可接受的盐作为腺苷A3受体激动剂，具有抑制炎症细胞（微胶质细胞、巨噬细胞和中性粒细胞等）向疾病部位的迁移和活化作用。此外，根据本发明的腺嘌呤衍生物在脑缺血实验模型中显示出明显抑制和治疗脑损伤的效果，即使在脑缺血后10小时内投药也显示出显著效果，并且已确认可延长脑缺血导致的脑损伤的生存时间，因此可用于治疗和预防包括脑卒中在内的退行性脑疾病，具有实用价值。

  公开号：

  KR20150010195A
• 作为产物：
  描述：

  2-chloro-N6-(3-iodobenzyl)-adenine 在 ammonium sulfate 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 83.0h， 生成 1-[2-氯-6-[[(3-碘苯基)甲基]氨基]-9h-嘌呤-9-基]-1-脱氧-N-甲基-beta-d-呋喃核糖酰胺
  参考文献：
  名称：

  N6-苄基腺苷-5'-糖醛酰胺的 2-取代增强了对 A3 腺苷受体的选择性。

  摘要：

  合成了带有 N6-(3-碘苄基) 基团的腺苷衍生物，据报道可增强腺苷-5'-糖醛酰胺类似物作为 A3 腺苷受体激动剂的亲和力 (J. Med. Chem. 1994, 37, 636-646)从甲基β-D-呋喃核苷开始，分10步。比较了大鼠脑膜中 A1 和 A2a 受体以及来自稳定转染的 CHO 细胞的克隆大鼠 A3 受体的结合亲和力。 N6-(3-碘苄基)腺苷对 A3 受体的选择性是 A1 或 A2a 受体的 2 倍；因此，它是第一个具有任何 A3 选择性的单取代腺苷类似物。探索了 2-取代与 N6-和 5'-位修饰相结合的效果。 2-氯-N6-(3-碘苄基)腺苷的 Ki 值为 1.4 nM，对 A3 受体具有中等选择性。 2-Chloro-N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide 的 Ki 值为 0.33 nM，对 A3 和 A1 和

  DOI：

  10.1021/jm00047a018

文献信息

• Purine nucleosides
  申请人：Jeong Shin Lak

  公开号：US20050256143A1

  公开（公告）日：2005-11-17

  Disclosed are purine nucleoside compounds that are selective to A 3 adenosine receptors and are useful for the treatment of cancer and inflammatory diseases. The compounds are shown by the following general formula (I), including isomers thereof: wherein X is sulfur or oxygen; R 1 is hydrogen, alkyl, benzyl, halobenzyl, or phenylalkyl; R 2 is hydrogen, halogen, alkoxy, alkenyl, alkynyl, alkylthio, or thio; R 3 and R 3′ are hydrogen, hydroxyalkyl, alkoxycarbonyl, or alkylaminocabonyl, whereas R 3 and R 3 ′ do not have identical substituents simultaneously; and R 4 is hydrogen or alkyl. Also disclosed are a pharmaceutical composition comprising a compound of formula (I), an isomer, or its pharmacologically acceptable salt as an active ingredient and a method for preventing or treating various diseases, state, or condition, including asthma, inflammation, cerebral ischemia, heart diseases, and cancer.

  揭示了对A3腺苷受体具有选择性的嘌呤核苷化合物，可用于治疗癌症和炎症性疾病。所述化合物由以下一般式（I）表示，包括其异构体：其中X为硫或氧；R1为氢、烷基、苄基、卤代苄基或苯基烷基；R2为氢、卤素、烷氧基、烯基、炔基、烷基硫基或硫基；R3和R3'为氢、羟基烷基、烷氧羰基或烷基氨羰基，其中R3和R3'不同时具有相同的取代基；R4为氢或烷基。还揭示了一种包含一种式（I）的化合物、其异构体或其药理学上可接受的盐作为活性成分的药物组合物，以及一种用于预防或治疗各种疾病、状态或症状的方法，包括哮喘、炎症、脑缺血、心脏疾病和癌症。
• Nucleoside Prodrugs of A3 Adenosine Receptor Agonists and Antagonists
  作者：Pedro Besada、Liaman K. Mamedova、Krishnan K. Palaniappan、Zhan-Guo Gao、Bhalchandra V. Joshi、Lak Shin Jeong、Mortimer M. Civan、Kenneth A. Jacobson

  DOI：10.1135/cccc20060912

  日期：——

  9-(β-D-Ribosfuranosyluronamide)adenine derivatives that are selective agonists and antagonists of the A₃ adenosine receptor (AR) have been derivatized as prodrugs for in vivo delivery. The free hydroxy groups at the 2' and 3' positions of the agonists 2-chloro-N⁶-(3-iodobenzyl)-9-(N-methyl-(β-D-ribosfuranosyluronamide)adenine 2b, the corresponding 4'-thio nucleoside 2c, and antagonists 4a and 4b (5'-N,N-dimethylamides related to 2b and 2c, respectively) were derivatized through simple acylation reactions. The prodrug derivatives were tested in radioligand binding assays at ARs and in a functional assay of adenylate cyclase at the A₃AR and found to be considerably less active than the parent drugs. The hydrolysis of nucleoside 2',3'-diesters to regenerate the parent compound in the presence of human blood was demonstrated. 2',3'-Dipropionate esters of 2b and 4a were readily cleaved in a two-step reaction to regenerate the parent drug, on a time scale of two hours. The cleavage of a 2',3'-dihexanoate ester occurred at a slower rate. This indicates that the prodrugs are suitable as masked forms of the biologically active A₃AR agonists and antagonists for future evaluation in vivo.

  9-(β-D-Ribosfuranosyluronamide)腺嘌呤衍生物被改造成为A3腺苷受体（AR）的选择性激动剂和拮抗剂的前药，用于体内输送。激动剂2-氯-N6-(3-碘苯甲基)-9-(N-甲基-(β-D-核糖呋喃脲酰脲)腺嘌呤2b，对应的4'-硫代核苷2c，以及拮抗剂4a和4b（分别与2b和2c相关的5'-N,N-二甲酰胺）的2'和3'位的游离羟基通过简单的酰基化反应进行了改造。在AR的放射配体结合测定和A3AR腺苷酸环化酶功能测定中，发现这些前药衍生物比原药物活性明显降低。在人类血液中证明了核苷2',3'-二酯的水解可以再生原药物。2',3'-二丙酸丙酯化合物2b和4a可以在两步反应中迅速裂解，再生原药物，时间尺度为两小时。2',3'-二己酸酯的裂解速率较慢。这表明这些前药适合作为生物活性A3AR激动剂和拮抗剂的掩蔽形式，以供未来体内评估。
• Design and in vivo activity of A3 adenosine receptor agonist prodrugs
  作者：R. Rama Suresh、Shanu Jain、Zhoumou Chen、Dilip K. Tosh、Yanling Ma、Maren C. Podszun、Yaron Rotman、Daniela Salvemini、Kenneth A. Jacobson

  DOI：10.1007/s11302-020-09715-0

  日期：2020.9

  normalized in the MRS7476-treated mice, but not liver fibrosis (no change in ACTA2 levels) or inflammation. Hepatic expression of ADORA3 in human NAFLD patients was 1.9-fold lower compared to normal controls. Adora3 expression determined by qPCR in primary mouse liver was associated with the stellate cells, and its mouse full body A3AR knockout worsened liver markers of inflammation and steatosis. Thus, we

  高选择性 A 3腺苷受体 (AR) 激动剂 Cl-IB-MECA 和 MRS5698 的前药（MRS7422、MRS7476）分别通过 2' 和 3' 羟基的琥珀酰化合成，母体活性药物显示与肝酯酶一起孵育后很容易释放。与母体 MRS5698 相比，前药 MRS7476 的水溶性大大增加，并且在逆转小鼠神经性疼痛（慢性缩窄性损伤模型，3 μmol/kg，po）（一种已知的 A 3 AR 效应）方面完全有效且持续时间比 MRS7422 更长。在 STAM 小鼠模型中，发现 MRS7476（5 毫克/千克，口服，每日两次）可预防非酒精性脂肪性肝炎 (NASH)，NAFLD 活动评分表明。在 MRS7476 治疗的小鼠中，肝细胞膨胀、IL-10 产生和肝脏组织学显着正常化，但肝纤维化（ACTA2 水平没有变化）或炎症没有正常化。人类 NAFLD 患者的ADORA3肝脏表达比正常对照低 1.9 倍。通过
• Structure-Activity Relationships of 9-Alkyladenine and Ribose-Modified Adenosine Derivatives at Rat A3 Adenosine Receptors
  作者：Kenneth A. Jacobson、Suhaib M. Siddiqi、Mark E. Olah、Xiao-duo Ji、Neli Melman、Kamala Bellamkonda、Yacov Meshulam、Gary L. Stiles、Hea O. Kim

  DOI：10.1021/jm00010a017

  日期：1995.5

  9-Alkyladenine derivatives and ribose-modified N-6-benzyladenosine derivatives were synthesized in an effort to identify selective ligands for the rat A(3) adenosine receptor and leads for the development of antagonists. The derivatives contained structural features previously determined to be important for A(3) selectivity in adenosine derivatives, such as an N-6-(3-iodobenzyl) moiety, and were further substituted at the 2-position with halo, amino, or thio groups. Affinity was determined in radioligand binding assays at rat brain A(3) receptors stably expressed in Chinese hamster ovary (CHO) cells, using [I-125]]AB-MECA (N-6-(4-amino-3-iodobenzyl)adenosine-5'-(N-methyluronamid)), and at rat brain A(1) and A(2a) receptors using [H-3]-N-6-PIA ((R)-N-6-phenylisopropyladenosine) and [H-3]CGS 21680 (2-[[[4-(2-carboxyethyl)-phenyl]ethyl]amino]-5'-(N-ethylcarbamoyl)adenosine), respectively. A series of N-6-(3-iodobenzyl) 2-amino derivatives indicated that a small 2-alkylamino group, e.g., methylamino, was favored at A(3) receptors. N-6-(3-Iodobenzyl)-9-methyl-2-(methylthio)adenine was 61-fold more potent than the corresponding 2-methoxy ether at A(3) receptors and of comparable affinity at A(1) and A(2a) receptors, resulting in a 3-6-fold selectivity for A(3) receptors. A pair of chiral N-6-(3-iodobenzyl) 9-(2,3-dihydroxypropyl) derivatives showed stereoselectivity, with the R-enantiomer favored at A(3) receptors by 5.7-fold. 2-Chloro-9-(beta-D-erythrofuranosyl)-N-6-(3-iodobenzyl)adenine had a K-i value at A(3) receptors of 0.28 mu M. 2-Chloro-9-[2-amino-2,3-dideoxy-beta-D-5-(methylcarbamoyl)-arabinofuranosyl]-N-6-(3-iodobenzyl)adenine was moderately selective for A(1) and A(3) VS A(2a) receptors. A 3'-deoxy analogue of a highly A(3)-selective adenosine derivative retained selectivity in binding and was a full agonist in the inhibition of adenylyl cyclase mediated via cloned rat A(3) receptors expressed in CHO cells. The 3'-OH and 4'-CH2OH groups of adenosine are not required for activation at A(3) receptors. A number of 2',3'-dideoxyadenosines and 9-acyclic-substituted adenines appear to inhibit adenylyl cyclase at the allosteric ''P'' site.
• J. Med. Chem. 1994, 37, 3614-3621
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  DOI：——

  日期：——